KR102293898B1 - Novel Triazine Derivatives and Thermo-curable or Photosensitive Composition Comprising the Same - Google Patents
Novel Triazine Derivatives and Thermo-curable or Photosensitive Composition Comprising the Same Download PDFInfo
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- KR102293898B1 KR102293898B1 KR1020190113485A KR20190113485A KR102293898B1 KR 102293898 B1 KR102293898 B1 KR 102293898B1 KR 1020190113485 A KR1020190113485 A KR 1020190113485A KR 20190113485 A KR20190113485 A KR 20190113485A KR 102293898 B1 KR102293898 B1 KR 102293898B1
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- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 150000003918 triazines Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 239000000178 monomer Substances 0.000 claims description 33
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 30
- 125000000732 arylene group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 7
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 claims description 7
- 229940125807 compound 37 Drugs 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims description 2
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims description 2
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims description 2
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 claims description 2
- 229940127007 Compound 39 Drugs 0.000 claims description 2
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 claims description 2
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims description 2
- 229940127573 compound 38 Drugs 0.000 claims description 2
- 229940126540 compound 41 Drugs 0.000 claims description 2
- 229940125936 compound 42 Drugs 0.000 claims description 2
- 229940125844 compound 46 Drugs 0.000 claims description 2
- 229940127271 compound 49 Drugs 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims description 2
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- -1 triazine derivative compound Chemical class 0.000 description 67
- 230000015572 biosynthetic process Effects 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 45
- 238000002360 preparation method Methods 0.000 description 36
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 14
- 125000004430 oxygen atom Chemical group O* 0.000 description 14
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- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 10
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- 125000005647 linker group Chemical group 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 7
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 7
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 6
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 6
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- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 6
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ZOPIKFDLIHWZLH-UHFFFAOYSA-N methanesulfonic acid hydroiodide Chemical compound I.CS(O)(=O)=O ZOPIKFDLIHWZLH-UHFFFAOYSA-N 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- GSJFXBNYJCXDGI-UHFFFAOYSA-N methyl 2-hydroxyacetate Chemical compound COC(=O)CO GSJFXBNYJCXDGI-UHFFFAOYSA-N 0.000 description 1
- AVVSSORVCLNBOS-UHFFFAOYSA-N methyl 2-propoxyacetate Chemical compound CCCOCC(=O)OC AVVSSORVCLNBOS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 150000002989 phenols Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- LVDAGIFABMFXSJ-UHFFFAOYSA-N propyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCC LVDAGIFABMFXSJ-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3236—Heterocylic compounds
- C08G59/3245—Heterocylic compounds containing only nitrogen as a heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 하기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물 및 이를 포함하는 감광성 조성물 또는 열경화성 조성물에 관한 것으로서, 상기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물의 구조는 발명의 상세한 설명에 기재된 바와 같다.The present invention relates to a compound represented by any one of the following [Formula A] to [Formula C] and a photosensitive composition or thermosetting composition comprising the same, wherein the structure of the compound represented by any one of [Formula A] to [Formula C] is as described in the detailed description of the invention.
Description
본 발명은 신규한 트리아진 유도체 및 이를 포함하는 열경화성 또는 감광성 조성물에 관한 것으로, 보다 상세하게는 열경화 또는 광가교 공정 이후의 굴절율이 높으며, 가교성 및 기계적 특성이 우수한 특성을 가지는, 신규한 트리아진 유도체 및 이를 포함하는 감광성 조성물에 관한 것이다.The present invention relates to a novel triazine derivative and a thermosetting or photosensitive composition comprising the same, and more particularly, a novel tree having a high refractive index after a thermosetting or photocrosslinking process, and excellent crosslinking and mechanical properties. It relates to an azine derivative and a photosensitive composition comprising the same.
액정표시장치(liquid crystal display, LCD)는 기재필름 및 기재필름 상에 형성된 광학패턴을 포함하는 광학시트를 포함하며, 광학시트 하부에는 도광판이 배치되거나 또는 광학시트와 도광판 사이에 또 다른 광학시트가 배치될 수 있다.A liquid crystal display (LCD) includes a base film and an optical sheet including an optical pattern formed on the base film, and a light guide plate is disposed under the optical sheet, or another optical sheet is disposed between the optical sheet and the light guide plate can be placed.
여기서, 광학시트의 종류로는 반사시트 (reflector sheet), 확산시트 (diffuser sheet), 프리즘 시트(prism sheet), 마이크로렌즈 등이 있으며, 이러한 광학시트는Here, the type of the optical sheet includes a reflector sheet, a diffuser sheet, a prism sheet, a microlens, and the like, and these optical sheets are
백라이트 유닛의 휘도를 향상시킬 목적으로 사용된다.It is used for the purpose of improving the luminance of the backlight unit.
광학시트는 백라이트의 도광판으로부터 나오는 광을 굴절시켜 액정을 통과한 후에 화면에 출사시키는 방식으로 출사되는 빛의 휘도를 증가시키며, 액정표시장치의 휘도를 높이기 위해서는 프리즘 및 DBEF 등의 광학시트의 굴절율이 높아야 한다.The optical sheet refracts the light emitted from the light guide plate of the backlight, passes through the liquid crystal, and then emits it to the screen to increase the luminance of the emitted light. should be high
특히, LCD 패널 제조기술이 발전함에 따라 얇고 휘도가 높은 LCD 디스플레이에 대한 요구가 높아졌고, 이에 따라 백라이트 유닛의 휘도를 높이려는 다양한 시도가 있어 왔다.In particular, with the development of LCD panel manufacturing technology, the demand for a thin and high luminance LCD display has increased, and accordingly, various attempts have been made to increase the luminance of the backlight unit.
또한 금속산화막 반도체(CMOS) 이미지센서(CIS), 첨단 디스플레이인 OLED의 봉지제 등에도 효율성 및 특성개선을 위해 고굴절 모노머 및 고굴절 재료의 사용이 증가하는 추세이다. In addition, the use of high-refractive monomers and high-refractive materials for improving efficiency and properties is also increasing for metal oxide semiconductor (CMOS) image sensors (CIS) and encapsulants for advanced displays, such as OLEDs.
그러나, 종래의 고굴절 모노머는 굴절율이 낮아 휘도 향상 효과를 구현하는데 한계가 있었으며, 또한 광학시트의 굴절률을 높이는 경우에도 광학시트에 황변 현상이 발생하는 등의 문제가 있었다. However, the conventional high refractive monomer has a low refractive index, so there is a limitation in realizing the effect of improving the luminance, and there is a problem such as yellowing occurs in the optical sheet even when the refractive index of the optical sheet is increased.
한편, 고굴절 모노머와 관련한 종래 기술로서, 한국등록특허공보 제10-2015-0118162호(2015.10.21) 및 한국공개특허공보 제10-2013-0081253호(2013.07.16)에서는 고굴절 모노머로써 에폭시 아크릴계 모노머, 티오에폭시 모노머 등을 제시하고 있고, 한국공개특허공보 제10-2019-0030167호(2019.03.21)에서는 고굴절 모노머로써 트리아진 유도체를 도입한 기술이 제시되어 있다.On the other hand, as a prior art related to a high refractive monomer, in Korea Patent Publication No. 10-2015-0118162 (2015.10.21) and Korean Patent Publication No. 10-2013-0081253 (2013.07.16), an epoxy acrylic monomer as a high refractive monomer .
그러나, 상기 선행기술들을 포함하는 종래기술에도 불구하고, 액정표시장치의 휘도 향상을 위해서 투과도와 내황변 특성이 우수하고, 높은 고굴절 특성을 가지며, 가교성 및 기계적 특성이 우수한 특성을 가지는 고굴절 모노머 재료가 요구되고 있는 실정이며, 따라서 새로운 고굴절 모노머의 개발 필요성은 지속적으로 요구되고 있다. However, in spite of the prior art including the prior art, a high refractive monomer material having excellent transmittance and yellowing resistance, high refractive index, and excellent crosslinking and mechanical properties for improving the luminance of a liquid crystal display device is required, and therefore, the need for the development of a new high refractive index monomer is continuously demanded.
따라서, 본 발명이 이루고자 하는 첫 번째 기술적 과제는 높은 투과도와, 우수한 광가교 특성 및 내황변 특성을 가지며, 특히 고굴절 특성을 가지는 열경화성 또는 감광성 조성물에 모노머로서 사용될 수 있는 반응 수축성이 매우 작고 기계적 성질이 우수한 특성의 신규한 트리아진 유도체 화합물을 제공하는 것이다. Therefore, the first technical problem to be achieved by the present invention is that it has high transmittance, excellent light crosslinking properties and yellowing resistance, and in particular, it has very small reaction shrinkage and mechanical properties that can be used as a monomer in a thermosetting or photosensitive composition having high refractive properties. An object of the present invention is to provide a novel triazine derivative compound with excellent properties.
또한, 본 발명에 따른 두 번째 기술적 과제는 상기 트리아진 유도체 화합물을 포함하는 열경화성 또는 감광성 조성물 및 이를 중합하여 얻어지는 광학 물품을 제공하는 것이다.In addition, a second technical problem according to the present invention is to provide a thermosetting or photosensitive composition comprising the triazine derivative compound and an optical article obtained by polymerizing the same.
상기 과제를 위해, 본 발명은 하기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물을 제공한다.For the above object, the present invention provides a compound represented by any one of the following [Formula A] to [Formula C].
[화학식 A][Formula A]
상기 [화학식 A]에서, In the [Formula A],
상기 L1 내지 L3은 각각 동일하거나 상이하며, 서로 독립적으로 단일결합, O, S, -N(-R1)-중에 선택된 어느 하나이며, The L 1 to L 3 are the same or different from each other, and are each independently any one selected from a single bond, O, S, -N(-R 1 )-,
상기 L1 내지 L3 중 2 이상이 각각 -N(-R1)- 를 선택하는 경우에 각각의 -N(-R1)- 는 동일하거나 상이하며,When two or more of L 1 to L 3 each select -N(-R 1 )-, each -N(-R 1 )- is the same or different,
상기 W1 내지 W3은 각각 동일하거나 상이하며, 서로 독립적으로 단일 결합, 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기 중에서 선택되는 어느 하나이고,Wherein W 1 To W 3 are the same or different, each independently selected from a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 1 -C 12 alkylene group is one,
상기 X1 내지 X3는 각각 동일하거나 상이하며, 서로 독립적으로 단일 결합, O, S, -N(-R2)- , -O((CH2)mO)n- 중에서 선택된 어느 하나이되, Wherein each of X 1 to X 3 are the same or different, and each independently a single bond, O, S, -N(-R 2 )- , -O((CH 2 ) m O) n - is any one selected from,
상기 m 및 n은 각각 동일하거나 상이하며, 서로 독립적으로 1 내지 4 중에서 선택되는 정수이고, Wherein m and n are the same or different from each other, and independently of each other are integers selected from 1 to 4,
상기 X1 내지 X3 중 2 이상이 각각 -N(-R2)- 를 선택하거나 또는 상기 X1 내지 X3 중 2 이상이 각각 -O((CH2)mO)n- 를 선택하는 경우에 각각의 -N(-R2)- 및 -O((CH2)mO)n- 는 각각 동일하거나 상이하며,Wherein X 1 to X 3 of two or more are each -N (-R 2) - or selected or the X 1 to X 3 is 2 or -O ((CH 2) m O ) of each of the n - when selecting a to each -N(-R 2 )- and -O((CH 2 ) m O) n - are each the same or different,
상기 R1 및 R2는 각각 동일하거나 상이하며, 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C50의 아릴기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C7-C24의 아릴알킬기 중에서 선택된 어느 하나이고,wherein R 1 and R 2 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C3- Any one selected from a C30 cycloalkyl group, a substituted or unsubstituted C7-C24 arylalkyl group,
상기 E1 내지 E3는 서로 동일하거나 상이하며, 서로 독립적으로 수소, 중수소 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C2-C30의 알케닐기, 치환 또는 비치환된 C2-C20의 알키닐기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C5-C30의 시클로알케닐기, 치환 또는 비치환된 C2-C50의 헤테로아릴기, 치환 또는 비치환된 C2-C30의 헤테로시클로알킬기, 치환 또는 비치환된 C1-C30의 알킬실릴기, 치환 또는 비치환된 C6-C30의 아릴실릴기 및 하기 [구조식 a] 또는 [구조식 b]로 표시되는 치환기 중에서 선택된 어느 하나이되,wherein E 1 to E 3 are the same as or different from each other, and independently of each other hydrogen, deuterium substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 of an alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 A heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, and the following [Structural formula a] or [ Any one selected from the substituents represented by Structural Formula b],
상기 E1 내지 E3 중 적어도 하나는 [구조식 a] 또는 [구조식 b]로 표시되는 치환기이고,At least one of E 1 to E 3 is a substituent represented by [Structural Formula a] or [Structural Formula b],
[구조식 a][Structural formula a]
[구조식 b][Structural formula b]
상기 [구조식 a] 및 [구조식 b]에서,In the [Structural Formula a] and [Structural Formula b],
상기 R4, R7 및 R11 은 각각 동일하거나 상이하며, 서로 독립적으로 치환 또는 비치환된 C1-C12의 알킬렌기, 치환 또는 비치환된 C6-C30의 아릴렌기 중에서 선택되는 어느 하나이고,Wherein R 4, R 7 and R 11 is one in which each the same or different and are each independently selected from a substituted or unsubstituted arylene group, a C1-C12 alkylene group, a substituted or unsubstituted C 6 -C 30 ,
상기 R5, R6, R8 내지 R10, R12 내지 R14 은 각각 동일하거나 상이하며, 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기 중에서 선택되는 어느 하나이며,The R 5 , R 6 , R 8 To R 10 , R 12 to R 14 are the same or different, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C1-C12 alkyl group,
상기 구조식 a 및 구조식 b 내 “-*”는 각각 상기 화학식 A내 X1 내지 X3 중에서 어느 하나와 결합되는 결합 사이트를 의미한다.“-*” in Structural Formulas a and b means a binding site bonded to any one of X 1 to X 3 in Formula A, respectively.
[화학식 B][Formula B]
[화학식 C][Formula C]
상기 [화학식 B] 에서, In the [Formula B],
상기 Ra는 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기 중에서 선택되는 어느 하나이며, Wherein Ra is any one selected from a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C1-C12 alkylene group,
상기 [화학식 C]에서, In the [Formula C],
상기 Ra'은 수소, 중수소, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기 중에서 선택되는 어느 하나이고,Wherein Ra' is any one selected from hydrogen, deuterium, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C1-C12 alkyl group,
상기 [화학식 B] 및 [화학식 C]에서, In the [Formula B] and [Formula C],
상기 L4 내지 L9는 각각 동일하거나 상이하며, 서로 독립적으로 단일 결합, O, S, -N(-R21)- 중에서 선택된 어느 하나이며,The L 4 to L 9 are the same or different from each other, and are each independently any one selected from a single bond, O, S, -N(-R 21 )-,
상기 L4 내지 L9 중 2 이상이 각각 -N(-R21)- 를 선택하는 경우에 각각의 -N(-R21)-는 동일하거나 상이하며,When two or more of L 4 to L 9 each select -N(-R 21 )-, each -N(-R 21 )- is the same or different,
상기 W4 내지 W7은 각각 동일하거나 상이하며, 서로 독립적으로 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기 중에서 선택되는 어느 하나이고,Each of W 4 to W 7 are the same or different, and are each independently selected from a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C1-C12 alkylene group,
상기 X4 내지 X7는 동일하거나 상이하며, 서로 독립적으로 O, S, -N(-R22)-, -O((CH2)mO)n- 중에서 선택된 어느 하나이되, Wherein X 4 To X 7 Are the same or different, and each independently be any one selected from O, S, -N(-R 22 )-, -O((CH 2 ) m O) n -,
상기 m 및 n은 각각 동일하거나 상이하며, 서로 독립적으로 1 내지 4 중에서 선택되는 정수이고, Wherein m and n are the same or different from each other, and independently of each other are integers selected from 1 to 4,
상기 X4 내지 X7 중 2 이상이 각각 -N(-R22)- 를 선택하거나 또는 상기 X4 내지 X7 중 2 이상이 각각 -O((CH2)mO)n-를 선택하는 경우에 각각의 -N(-R22)- 및 -O((CH2)mO)n-는 각각 동일하거나 상이하며,When two or more of X 4 to X 7 each select -N(-R 22 )-, or two or more of X 4 to X 7 each select -O((CH 2 ) m O) n - to each -N(-R 22 )- and -O((CH 2 ) m O) n - are each the same or different,
상기 R21 및 R22는 각각 동일하거나 상이하며, 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C50의 아릴기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C7-C24의 아릴알킬기 중에서 선택된 어느 하나이고,wherein R 21 and R 22 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C3- Any one selected from a C30 cycloalkyl group, a substituted or unsubstituted C7-C24 arylalkyl group,
상기 E4 내지 E7는 서로 동일하거나 상이하며, 서로 독립적으로 수소, 중수소 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C2-C30의 알케닐기, 치환 또는 비치환된 C2-C20의 알키닐기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C5-C30의 시클로알케닐기, 치환 또는 비치환된 C2-C50의 헤테로아릴기, 치환 또는 비치환된 C2-C30의 헤테로시클로알킬기, 치환 또는 비치환된 C1-C30의 알킬실릴기, 치환 또는 비치환된 C6-C30의 아릴실릴기 및 하기 [구조식 a] 또는 [구조식 b]로 표시되는 치환기 중에서 선택된 어느 하나이되, E 4 to E 7 are the same as or different from each other, and independently of each other hydrogen, deuterium substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 of an alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 A heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, and the following [Structural formula a] or [ Any one selected from the substituents represented by Structural Formula b],
상기 E4 내지 E7 중 적어도 하나는 [구조식 a] 또는 [구조식 b]로 표시되는 치환기이고,At least one of E4 to E7 is a substituent represented by [Structural formula a] or [Structural formula b],
[구조식 a][Structural formula a]
[구조식 b][Structural formula b]
상기 [구조식 a] 및 [구조식 b]에서,In the [Structural Formula a] and [Structural Formula b],
상기 R4, R7 및 R11 은 각각 동일하거나 상이하며, 서로 독립적으로 치환 또는 비치환된 C1-C12의 알킬렌기, 치환 또는 비치환된 C6-C30의 아릴렌기 중에서 선택되는 어느 하나이고,Wherein R 4, R 7 and R 11 is one in which each the same or different and are each independently selected from a substituted or unsubstituted arylene group, a C1-C12 alkylene group, a substituted or unsubstituted C 6 -C 30 ,
상기 R5, R6, R8 내지 R10, R12 내지 R14 은 각각 동일하거나 상이하며, 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기 중에서 선택되는 어느 하나이며,The R 5 , R 6 , R 8 To R 10 , R 12 to R 14 are the same or different, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C1-C12 alkyl group,
상기 구조식 a 및 구조식 b 내 “-*”는 각각 상기 화학식 B 및 화학식 C 내 X4 내지 X7 중에서 어느 하나와 결합되는 결합 사이트를 의미한다.“-*” in Structural Formulas a and b means a binding site bonded to any one of X 4 to X 7 in Formulas B and C, respectively.
통상적으로 트리아진 화합물은 굴절율이 높은 특성임에도 불구하고, 유도체의 구조에 에폭시수지의 개시제 특성을 갖는 '-NH-'기를 가지고 있어, 트리아진 고유의 가교성 및 기계적 특성이 우수함에도 불구하고 모노머의 말단 등에 에폭시기를 도입하기 어려운 한계를 보여주고 있었으나, 본 발명에서는 에피클로히드린 및 강염기의 당량을 적절히 조절하여 에폭시수지의 개시제 특성을 갖는 '-NH-'기를 포함하는 트리아진 구조를 분자내에 가지면서도 또한 분자내 말단에 에폭시기를 포함하는 신규한 모노머를 합성할 수 있었고, 이를 통해 굴절율이 높은 트리아진 유도체의 말단에 반응수축성이 매우 작고 기계적 성질이 우수한 에폭시수지를 도입한 모노머를 제공할 수 있는 장점을 가진다.In general, triazine compounds have a '-NH-' group having the initiator characteristics of an epoxy resin in the structure of the derivative, despite the high refractive index properties, so that, despite the excellent crosslinking and mechanical properties inherent in triazine, the monomer Although it was difficult to introduce an epoxy group at the terminal, etc., in the present invention, by appropriately adjusting the equivalents of epichlorohydrin and a strong base, a triazine structure including a '-NH-' group having the initiator properties of the epoxy resin has in the molecule. In addition, it was possible to synthesize a new monomer containing an epoxy group at the end of the molecule, and through this, it was possible to provide a monomer that introduced an epoxy resin with very small reaction shrinkage and excellent mechanical properties at the end of the triazine derivative having a high refractive index. have an advantage
또한, 본 발명에 따른 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 신규한 트리아진 유도체 화합물은 열가교 및/또는 감광성 조성물에 이용되어 굴절율이 높은 특성뿐만 아니라 가교성이 우수하고, 기계적 성질이 우수한 특성을 제공할 수 있다. In addition, the novel triazine derivative compound represented by any one of [Formula A] to [Formula C] according to the present invention is used for thermal crosslinking and/or photosensitive composition and has excellent crosslinking properties as well as high refractive index properties, mechanical Properties can provide excellent properties.
특히, 높은 투과도와 내황변 특성이 우수한 감광성 조성물을 제공할 수 있어, 종래 기술에 따른, 굴절율이 낮아 휘도 향상 효과를 구현하는데 한계가 있고, 황변현상으로 인해 광학시트의 색변화되는 문제를 해결할 수 있는 효과가 있어, 프리즘 시트, 마이크로렌즈, LCD용 코팅 재료, DBEF(Dual Brightness Enhancement Film) 필름, TFT-LCD용 코팅 재료, 유기발광소자(OLED)용 코팅 재료, 광학렌즈, 다초점렌즈 등의 제조를 위한 용도에 적용 가능한 장점이 있다.In particular, it is possible to provide a photosensitive composition having high transmittance and excellent yellowing resistance, so there is a limitation in realizing the luminance improvement effect due to the low refractive index according to the prior art, and it is possible to solve the problem of color change of the optical sheet due to yellowing. prism sheet, microlens, coating material for LCD, DBEF (Dual Brightness Enhancement Film) film, coating material for TFT-LCD, coating material for organic light emitting device (OLED), optical lens, multifocal lens, etc. There are advantages that can be applied to uses for manufacturing.
이하, 본 발명을 더욱 상세하게 설명한다. 다른 식으로 정의되지 않는 한, 본 명세서에서 사용된 모든 기술적 및 과학적 용어들은 본 발명이 속하는 기술분야에서 숙련된 전문가에 의해서 통상적으로 이해되는 것과 동일한 의미를 가진다. 일반적으로, 본 명세서에서 사용된 명명법은 본 기술분야에서 잘 알려져 있고 통상적으로 사용되는 것이다.Hereinafter, the present invention will be described in more detail. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In general, the nomenclature used herein is those well known and commonly used in the art.
본원 명세서 전체에서, 어떤 부분이 어떤 구성 요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성 요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미한다.Throughout this specification, when a part "includes" a certain component, it means that other components may be further included, rather than excluding other components, unless otherwise stated.
본 발명에 따른 상기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물은 분자내에 1 내지 3개의 트리아진 구조를 포함하며, 트리아진의 각각의 탄소원자에 N, O, S, 또는 단일결합을 가지는 제1연결부분; 단일결합, 알킬렌기 또는 아릴렌기를 포함하는 제2연결부분; 및 N, O, S, 알킬렌옥사이드 또는 단일결합을 가지는 제3연결부분;을 포함하며, 말단에 적어도 하나 이상의 에폭시 구조로서, 상기 [구조식 a] 또는 [구조식 b]로 표시되는 치환기를 포함하는 구조를 갖는 것을 기술적 특징으로 한다. The compound represented by any one of [Formula A] to [Formula C] according to the present invention includes 1 to 3 triazine structures in the molecule, and N, O, S, or single at each carbon atom of the triazine a first connecting portion having a bond; a second connection portion including a single bond, an alkylene group, or an arylene group; And N, O, S, an alkylene oxide or a third connecting portion having a single bond; as at least one epoxy structure at the terminal, comprising a substituent represented by the [Structural formula a] or [Structural formula b] It is characterized in that it has a structure.
여기서, 상기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 트리아진 화합물을 포함하는 감광성 조성물을 모노머로서 사용하는 경우, 굴절율과 투과도가 높고 우수한 내황변 특성뿐 아니라, 가교성 및 기계적 특성이 우수한 성질을 나타낼 수 있다. Here, when the photosensitive composition containing the triazine compound represented by any one of the above [Formula A] to [Formula C] is used as a monomer, the refractive index and transmittance are high and excellent yellowing resistance, as well as crosslinking and mechanical properties It can exhibit excellent properties.
한편, 본 발명에서의 상기 “치환 또는 비치환된 C1-C20의 알킬기”, “치환 또는 비치환된 C6-C50의 아릴기” 등에서의 상기 알킬기 또는 아릴기의 범위를 고려하여 보면, 상기 C1-C20의 알킬기 및 C6-C50의 아릴기의 탄소수의 범위는 각각 상기 치환기가 치환된 부분을 고려하지 않고 비치환된 것으로 보았을 때의 알킬 부분 또는 아릴 부분을 구성하는 전체 탄소수를 의미하는 것이다. 예컨대, 파라위치에 부틸기가 치환된 페닐기는 C4의 부틸기로 치환된 C6의 아릴기에 해당하는 것으로 보아야 한다. On the other hand, when considering the range of the alkyl group or aryl group in the "substituted or unsubstituted C 1 -C 20 alkyl group", "substituted or unsubstituted C 6 -C 50 aryl group" in the present invention, , The range of carbon number of the C 1 -C 20 alkyl group and the C 6 -C 50 aryl group is the total constituting the alkyl portion or the aryl portion when viewed as unsubstituted without considering the portion substituted with the substituent. It means carbon number. For example, a phenyl group substituted with a butyl group at the para-position should be considered to correspond to a C 6 aryl group substituted with a C 4 butyl group.
본 발명의 화합물에서 사용되는 치환기인 아릴기는 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 5 내지 7원, 바람직하게는 5 또는 6원을 포함하는 단일 또는 융합고리계를 포함하며, 또한 상기 아릴기에 치환기가 있는 경우 이웃하는 치환기와 서로 융합 (fused)되어 고리를 추가로 형성할 수 있다.The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, In addition, when the aryl group has a substituent, it may be fused with a neighboring substituent to further form a ring.
상기 아릴기의 구체적인 예로는 페닐기, o-비페닐기, m-비페닐기, p-비페닐기, o-터페닐기, m-터페닐기, p-터페닐기, 나프틸기, 안트릴기, 페난트릴기, 피레닐기, 인데닐, 플루오레닐기, 테트라히드로나프틸기, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일등과 같은 방향족 그룹을 들 수 있고, 상기 아릴기 중 하나 이상의 수소 원자는 중수소 원자, 할로겐 원자, 히드록시기, 니트로기, 시아노기, 실릴기, 아미노기 (-NH2, -NH(R), -N(R')(R''), R'과 R"은 서로 독립적으로 C1-C10의 알킬기이며, 이 경우 "알킬아미노기"라 함), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, C1-C24의 알킬기, C1-C24의 할로겐화된 알킬기, C2-C24의 알케닐기, C2-C24의 알키닐기, C1-C24의 헤테로알킬기, C6-C24의 아릴기, C7-C24의 아릴알킬기, C2-C24의 헤테로아릴기 또는 C2-C24의 헤테로아릴알킬기로 치환될 수 있다.Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, and aromatic groups such as pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., wherein at least one hydrogen atom of the aryl group is a deuterium atom, halogen Atom, hydroxyl group, nitro group, cyano group, silyl group, amino group (-NH2, -NH(R), -N(R')(R''), R' and R" are independently of each other C 1 -C 10 of an alkyl group, in this case referred to as "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C 1 -C 24 alkyl group, C 1 -C 24 halogenated alkyl group, C 2- C 24 Alkenyl group, C 2 -C 24 Alkynyl group, C 1 -C 24 Heteroalkyl group, C 6 -C 24 Aryl group, C 7 -C 24 Arylalkyl group, C 2 -C 24 It may be substituted with a heteroaryl group or a C 2 -C 24 heteroarylalkyl group.
본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기는 아릴기에서 N, O, P, Si, S, Ge, Se, Te 중에서 선택된 1, 2 또는 3개의 헤테로 원자를 포함하고, 나머지 고리 원자가 탄소인 C2-C24의 고리 방향족 시스템을 의미하며, 상기 고리들은 융합(fused)되어 고리를 형성할 수 있다. 그리고 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.The heteroaryl group as a substituent used in the compound of the present invention includes 1, 2 or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in the aryl group, and the remaining ring atoms are C It refers to a ring aromatic system of 2- C 24 , and the rings may be fused to form a ring. And one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituents as in the case of the aryl group.
또한 본 발명에서 사용되는 치환기인 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, 이소프로필, 이소부틸, sec-부틸, tert-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있고, 상기 알킬기 중 하나 이상의 수소 원자는 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.In addition, specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like, and one of the alkyl groups The above hydrogen atoms can be substituted with the same substituents as in the case of the aryl group.
본 발명의 화합물에서 사용되는 치환기인 알콕시기의 구체적인 예로는 메톡시, 에톡시, 프로폭시, 이소부틸옥시, sec-부틸옥시, 펜틸옥시, iso-아밀옥시, 헥실옥시 등을 들 수 있고, 상기 알콕시기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkoxy group as a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy and the like, One or more hydrogen atoms in the alkoxy group may be substituted with the same substituents as in the case of the aryl group.
본 발명의 화합물에서 사용되는 치환기인 알킬아릴기의 구체적인 예로는 메틸페닐, 디메틸페닐, n-프로필페닐, t-부틸페닐, 메틸나프틸 등을 들 수 있고, 상기 알킬아릴기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkylaryl group as a substituent used in the compound of the present invention include methylphenyl, dimethylphenyl, n -propylphenyl, t -butylphenyl, methylnaphthyl, and the like, and at least one hydrogen atom in the alkylaryl group is It may be substituted with the same substituents as in the case of the aryl group.
본 발명의 화합물에서 사용되는 치환기인 시클로알킬기의 구체적인 예로는 시클로부틸, 시클로펜틸, 시클로헥실, 메틸시클로펜틸, 메틸시클로헥실, 에틸시클로펜틸, 에틸시클로헥실 등을 들 수 있고, 상기 시클로알킬기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능 하다.Specific examples of the cycloalkyl group as a substituent used in the compound of the present invention include cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, and the like, and one of the cycloalkyl groups The above hydrogen atoms can be substituted with the same substituents as in the case of the aryl group.
본 발명의 화합물에서 사용되는 치환기인 실릴기의 구체적인 예로는 트리메틸실릴, 트리에틸실릴, 트리페닐실릴, 트리메톡시실릴, 디메톡시페닐실릴, 디페닐메틸실릴, 디페닐비닐실릴, 메틸사이클로뷰틸실릴, 디메틸퓨릴실릴 등을 들 수 있고, 상기 실릴기 중 하나 이상의 수소 원자는 상기 아릴기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the silyl group as a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , dimethylfurylsilyl, and the like, wherein one or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.
한편, 본 발명에 따른 상기 화학식 A로 표시되는 화합물 내 상기 L1 내지 L3은 각각 동일하거나 상이하며, 서로 독립적으로 단일결합, O, S,-N(-R1)-중에 선택된 어느 하나이며, 상기 L1 내지 L3 중 2 이상이 각각 -N(-R1)- 를 선택하는 경우에 각각의 -N(-R1)- 는 동일하거나 상이하며, 상기 R1은 수소, 중수소, 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C50의 아릴기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C7-C24의 아릴알킬기 중에서 선택된 어느 하나일 수 있는 바, 이때, 바람직하게는 상기 화학식 A내 상기 L1 내지 L3 중에서 2 이상은 각각 S 또는 -N(-R1)- 이고, 상기 R1은 수소, 중수소, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기에서 선택되는 어느 하나일 수 있고, 여기서, 상기 L1 내지 L3 중에서 2 이상이 -N(-R1)- 인 경우에 각각의 -N(-R1)-는 각각 동일하거나 상이하며, 이 경우 투과도가 우수하면서도 굴절율이 높은 특성을 가질 수 있으며, 더욱 바람직하게는, 상기 화학식 A내 상기 L1 내지 L3 은 각각 동일하거나 상이하며, 서로 독립적으로 모두가 S 또는 -N(-R1)- 일 수 있으며, 여기서, 상기 L1 내지 L3 중에서 2 이상이 -N(-R1)- 인 경우에 각각의 -N(-R1)-는 각각 동일하거나 상이하다.Meanwhile, in the compound represented by Formula A according to the present invention, L 1 to L 3 are the same or different, and are each independently selected from a single bond, O, S, -N(-R 1 )-, and , When two or more of L 1 to L 3 each select -N(-R 1 )-, each -N(-R 1 )- is the same or different, and R 1 is hydrogen, deuterium, substituted Or any one selected from an unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C3-C30 cycloalkyl group, and a substituted or unsubstituted C7-C24 arylalkyl group In this case, preferably , two or more of L 1 to L 3 in Formula A are S or -N(-R 1 )-, respectively, and R 1 is hydrogen, deuterium, substituted or unsubstituted C It may be any one selected from a 6 -C 30 aryl group, a substituted or unsubstituted C1-C12 alkyl group, wherein two or more of L 1 to L 3 are -N(-R 1 )- Each -N(-R 1 )- is the same or different from each other, and in this case, the transmittance is excellent and the refractive index is high, and more preferably, L 1 to L 3 in Formula A are each the same or different, and all independently of each other may be S or -N(-R 1 )-, wherein, among L 1 to L 3 , each -N when at least two are -N(-R 1 )- (-R 1 )- is the same or different from each other.
또한, 상기 [화학식 A]에서, 상기 R1는 각각 수소 또는 중수소일 수 있으며, 이때, 바람직하게는 상기 트리아진의 탄소원자 3개 중에 적어도 하나의 탄소원자에는 연결기로서 -NH-기가 결합되고, 더욱 바람직하게는 2개이상의 -NH-기가 결합될 수 있다.In addition, in [Formula A], R 1 may be hydrogen or deuterium, respectively, Preferably, a -NH- group may be bonded as a linking group to at least one carbon atom among three carbon atoms of the triazine, and more preferably, two or more -NH- groups may be bonded.
또한, 본 발명에서의 상기 화학식 A내 상기 W1 내지 W3은 각각 동일하거나 상이하며, 서로 독립적으로 단일 결합, 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기 중에서 선택되는 어느 하나일 수 있으며, 바람직하게는 상기 화학식 A내 상기 W1 내지 W3 중에서 적어도 하나는 치환 또는 비치환된 C6-C30의 아릴렌기일 수 있고, 더욱 바람직하게는, 상기 W1 내지 W3 중에서 2 이상이 치환 또는 비치환된 C6-C30의 아릴렌기이거나 또는 상기 W1 내지 W3 모두 치환 또는 비치환된 C6-C30의 아릴렌기일 수 있다. In addition, in Formula A in the present invention, W 1 to W 3 are the same or different, and are each independently a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C1- It may be any one selected from a C12 alkylene group, and preferably , at least one of W 1 to W 3 in Formula A may be a substituted or unsubstituted C 6 -C 30 arylene group, more preferably is, two or more of W1 to W 3 may be a substituted or unsubstituted C 6 -C 30 arylene group, or all of W 1 to W 3 may be a substituted or unsubstituted C 6 -C 30 arylene group.
이 경우에 상기 C6-C30의 아릴렌기의 아로마틱 평면구조와 트리아진의 평면 구조로 인하여 판상구조를 형성하여 이로 인하여 높은 고굴절 특성이 나타날 수 있는 것으로 추정된다. In this case, it is estimated that a plate-like structure may be formed due to the aromatic planar structure of the C 6 -C 30 arylene group and the planar structure of the triazine, thereby exhibiting high refractive properties.
예컨대, 상기 화학식 A내 상기 W1 내지 W3 중에서 적어도 하나는 치환 또는 비치환된 C6-C30의 아릴렌기의 구체적인 예로서, 상기 화학식 A내 상기 W1은 치환 또는 비치환된 페닐렌기이고, 상기 W2 및 W3는 동일하거나 상이하며, 서로 독립적으로 단일결합, 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기일 수 있다.For example, at least one of W 1 to W 3 in Formula A is a specific example of a substituted or unsubstituted C 6 -C 30 arylene group, and W 1 in Formula A is a substituted or unsubstituted phenylene group, , W 2 and W 3 may be the same or different, and independently of each other may be a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 1 -C 12 alkylene group.
또한, 상기 W1 내지 W3 중에서 2 이상이 치환 또는 비치환된 C6-C30의 아릴렌기인 경우의 구체적인 예로서, 상기 W1은 치환 또는 비치환된 페닐렌기이고, 상기 W2 및 W3는 동일하거나 상이하며, 이들 중 적어도 하나는 치환 또는 비치환된 C6-C30의 아릴렌기인 경우와, 상기 W1 내지 W3 는 각각 동일하거나 상이하며, 이들 중 적어도 2개는 치환 또는 비치환된 페닐렌기인 경우를 들 수 있으며, 또는, 상기 W1 내지 W3 는 각각 동일하거나 상이하며, 모두가 치환 또는 비치환된 페닐렌기인 경우를 들 수 있다.In addition, as a specific example when two or more of W 1 to W 3 are a substituted or unsubstituted C 6 -C 30 arylene group, W 1 is a substituted or unsubstituted phenylene group, and W 2 and W 3 are the same or different, and at least one of them is a substituted or unsubstituted C 6 -C 30 arylene group, and W 1 to W 3 are the same or different, and at least two of them are substituted or It may be an unsubstituted phenylene group, or W 1 to W 3 are the same or different, and all may be a substituted or unsubstituted phenylene group.
또한, 본 발명에서의 상기 화학식 A내 상기 X1 내지 X3는 각각 동일하거나 상이하며, 서로 독립적으로 단일 결합, O, S, -N(-R2)-, -O((CH2)mO)n- 중에서 선택된 어느 하나일 수 있고, 이때, 상기 m 및 n은 각각 동일하거나 상이하며, 서로 독립적으로 1 내지 4 중에서 선택되는 정수이고, 상기 X1 내지 X3 중 2 이상이 각각 -N(-R2)- 를 선택하거나 또는 상기 X1 내지 X3 중 2 이상이 각각 -O((CH2)mO)n- 를 선택하는 경우에 각각의 -N(-R2)- 및 -O((CH2)mO)n- 는 각각 동일하거나 상이하며,In addition, in Formula A in the present invention, X 1 to X 3 are the same or different, and each independently a single bond, O, S, -N(-R 2 )-, It may be any one selected from -O((CH 2 ) m O) n -, wherein m and n are the same or different from each other, and each independently represent an integer selected from 1 to 4, and the X 1 to X each -N when at least two of 3 select -N(-R 2 )- or at least 2 of X 1 to X 3 each select -O((CH 2 ) m O) n - (-R 2 )- and -O((CH 2 ) m O) n - are each the same or different,
상기 R2는 수소, 중수소, 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C50의 아릴기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C7-C24의 아릴알킬기 중에서 선택된 어느 하나일 수 있다.R 2 is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C7- It may be any one selected from a C24 arylalkyl group.
또한, 본 발명에서의 상기 화학식 A내 X1 내지 X3 중 적어도 1개는 산소원자(O)일 수 있고, 이 경우 화학식 A로 표시되는 화합물로부터 제조된 감광성 조성물 또는 열경화성 조성물은 가교성 및 기계적 특성이 우수한 특성을 가질 수 있으며, 바람직하게는 X1 내지 X3 중 적어도 2개는 산소원자(O)일 수 있다. In addition, at least one of X 1 to X 3 in Formula A in the present invention may be an oxygen atom (O), and in this case, the photosensitive composition or thermosetting composition prepared from the compound represented by Formula A is crosslinkable and mechanically It may have excellent properties, and preferably , at least two of X 1 to X 3 may be an oxygen atom (O).
한편, 본 발명에서의 상기 화학식 A내 상기 X1 내지 X3 중 적어도 하나가 산소원자(-O- )이며, 이와 동시에 상기 산소원자와 결합되는 W1 또는 W2 또는 W3 이 치환 또는 비치환 페닐렌기에 해당하는 경우에, 상기 산소원자는 연결기 L(L1 내지 L3)을 기준으로 오르쏘 또는 메타위치에 결합될 수 있다. Meanwhile, at least one of X 1 to X 3 in Formula A in the present invention is an oxygen atom (-O- ), and at the same time, W 1 or W 2 or W 3 bonded to the oxygen atom is substituted or unsubstituted In the case of a phenylene group, the oxygen atom may be bonded to an ortho or meta position based on the linking group L (L 1 to L 3 ).
이는 상기 W1 또는 W2 또는 W3 이 치환 또는 비치환 페닐렌기에 해당하는 경우에 이들에 결합하는 산소원자가 파라위치에 결합하는 경우에 얻어지는 화합물의 용해도가 낮아져 조성물에서 결정이 석출되는 문제점을 내포하기 때문으로서, 본 발명에서는 상기 산소원자를 연결기 L(L1 내지 L3)을 기준으로 오르쏘 또는 메타위치에 결합된 화합물을 사용하여 이를 해소할 수 있다.This includes a problem in that, when W 1 or W 2 or W 3 corresponds to a substituted or unsubstituted phenylene group, the solubility of the compound obtained is lowered when the oxygen atom bonded thereto is bonded to the para position, thereby precipitating crystals from the composition. As such, in the present invention, this can be solved by using a compound in which the oxygen atom is bonded to the ortho or meta position based on the linking group L (L 1 to L 3 ).
즉, 본 발명에 따른 상기 화학식 A로 표시되는 화합물은, 상기 X1는 -O- 이고, 상기 W1이 치환 또는 비치환 페닐렌기이며, 이때, 상기 X1은 L1을 기준으로 오르쏘 또는 메타 위치에 치환되거나; 또는, 상기 X2는 -O- 이고, 상기 W2이 치환 또는 비치환 페닐렌기이며, 이때, 상기 X2은 L2을 기준으로 오르쏘 또는 메타 위치에 치환되거나; 또는, 상기 X3는 -O- 이고, 상기 W3이 치환 또는 비치환 페닐렌기이며, 이때, 상기 X3은 L3을 기준으로 오르쏘 또는 메타 위치에 치환되는 화합물이 사용되는 것이 바람직하다.That is, in the compound represented by Formula A according to the present invention, wherein X 1 is -O-, and W 1 is a substituted or unsubstituted phenylene group, in this case, X 1 is ortho ortho based on L 1 substituted at the meta position; Alternatively, X 2 is —O—, and W 2 is a substituted or unsubstituted phenylene group, wherein X 2 is ortho or meta-substituted with respect to L 2 ; Alternatively, X 3 is -O-, and W 3 is a substituted or unsubstituted phenylene group, in this case, wherein X 3 is preferably a compound substituted at an ortho or meta position with respect to L 3 .
한편, 본 발명에서의 화학식 B 는 두 개의 트리아진 고리가 연결기 '-L8-Ra-L9-'를 통해 서로 연결되어 있으며, 각각의 트리아진 고리는 상기 화학식 A에서와 유사한 구조로서 상기 화학식 B내 적어도 하나 이상의 에폭시기를 말단에 포함하는 구조를 기술적 특징으로 하며, 또한 상기 화학식 C는 두 개의 트리아진 고리가 연결기 'N-Ra'-'를 통해 서로 연결되어 있으며, 각각의 트리아진 고리는 상기 화학식 A에서와 유사한 구조로서 상기 화학식 C내 적어도 하나 이상의 에폭시기를 말단에 포함하는 구조를 기술적 특징으로 한다. On the other hand, in Formula B in the present invention, two triazine rings are connected to each other through a linking group '-L 8 -Ra-L 9 -', and each triazine ring has a structure similar to that in Formula A, It is technically characterized by a structure including at least one epoxy group in B at the terminal, and in Formula C, two triazine rings are connected to each other through a linking group 'N-Ra'-', and each triazine ring is As a structure similar to that in Chemical Formula A, a structure including at least one epoxy group in Chemical Formula C at a terminal thereof is technically characterized.
또한, 본 발명에서의 상기 [화학식 B] 및 [화학식 C]에서, 바람직하게는 상기 L4 내지 L7 중에서 2 이상은 각각 S 또는 -N(-R21)- 이고, 상기 R21은 수소, 중수소, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기에서 선택되는 어느 하나일 수 있고, 여기서, 상기 L4 내지 L7 중에서 2 이상이 -N(-R21)- 인 경우에 각각의 -N(-R21)-는 각각 동일하거나 상이할 수 있으며, 이경우에 투과도가 우수하면서도 굴절율이 높은 특성을 가질 수 있으며, 더욱 바람직하게는 상기 [화학식 B] 및 [화학식 C]에서의 상기 L4 내지 L7 은 각각 동일하거나 상이하며, 서로 독립적으로 모두가 S 또는 -N(-R21)- 일 수 있으며, 여기서, 상기 L4 내지 L7 중에서 2 이상이 -N(-R21)- 인 경우에 각각의 -N(-R21)-는 각각 동일하거나 상이하다.In addition, in the [Formula B] and [Formula C] in the present invention, preferably , two or more of L 4 to L 7 are S or -N(-R 21 )-, respectively, and R 21 is hydrogen, It may be any one selected from deuterium, a substituted or unsubstituted C 6 -C 30 aryl group, and a substituted or unsubstituted C1-C12 alkyl group, wherein two or more of L 4 to L 7 are -N ( In the case of -R 21 )-, each -N(-R 21 )- may be the same or different, and in this case, it may have excellent transmittance and high refractive index, and more preferably the [Formula B ] and L 4 to L 7 in [Formula C] are the same or different from each other, and all independently of each other may be S or -N(-R 21 )-, wherein 2 of L 4 to L 7 When more than one is -N(-R 21 )-, each -N(-R 21 )- is each the same or different.
또한, 상기 [화학식 B] 및 [화학식 C]에서, 상기 R21는 각각 수소 또는 중수소일 수 있으며, 이때, 바람직하게는 상기 트리아진의 탄소원자 3개 중에 적어도 하나의 탄소원자에는 연결기로서 -NH-기가 결합되고, 더욱 바람직하게는 2개이상의 -NH-기가 결합될 수 있다.In addition, in [Formula B] and [Formula C], R 21 may each be hydrogen or deuterium, and in this case, preferably at least one carbon atom among three carbon atoms of the triazine is -NH as a linking group A -group may be bonded, and more preferably, two or more -NH- groups may be bonded.
또한 본 발명에서의 상기 [화학식 B] 및 [화학식 C]내 상기 W4 내지 W7은 각각 동일하거나 상이하며, 서로 독립적으로 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기 중에서 선택되는 어느 하나일 수 있으며, 바람직하게는 상기 W4 내지 W7 중 2 이상은 치환 또는 비치환된 C6-C30의 아릴렌기이거나 또는, W4 내지 W7 중에서 3 이상은 치환 또는 비치환된 C6-C30의 아릴렌기이거나, 또는 W4 내지 W7 모두 치환 또는 비치환된 C6-C30의 아릴렌기일 수 있다.In addition, in the [Formula B] and [Formula C] in the present invention, W 4 to W 7 are the same or different, and each independently a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted may be any one selected from among C1-C12 alkylene groups, preferably at least two of W 4 to W 7 are substituted or unsubstituted C 6 -C 30 arylene groups, or W 4 to W 7 3 or more may be a substituted or unsubstituted C 6 -C 30 arylene group, or all of W 4 to W 7 may be a substituted or unsubstituted C 6 -C 30 arylene group.
이 경우에 화학식 A에서와 마찬가지로, 상기 [화학식 B] 및 [화학식 C]에서의 상기 C6-C30의 아릴렌기의 아로마틱 평면구조와 트리아진의 평면 구조로 인하여 판상구조를 형성하여 이로 인하여 높은 고굴절 특성이 나타날 수 있는 것으로 추정된다. In this case, as in Formula A, a plate-like structure is formed due to the aromatic planar structure of the C 6 -C 30 arylene group and the planar structure of the triazine in the [Formula B] and [Formula C]. It is estimated that high refractive properties may appear.
예컨대, 상기 [화학식 B] 및 [화학식 C]에서의 W4 내지 W7 중에서 2 이상이 치환 또는 비치환된 C6-C30의 아릴렌기인 경우의 구체적인 예로서, 상기 W4 내지 W7 중에서 2 이상이 치환 또는 비치환된 페닐렌기일 수 있다.For example, as a specific example when two or more of W 4 to W 7 in [Formula B] and [Formula C] are substituted or unsubstituted C 6 -C 30 arylene groups, among W 4 to W 7 Two or more may be a substituted or unsubstituted phenylene group.
이 경우에, 상기 W4 내지 W7 중 페닐렌기가 아닌 나머지는 동일하거나 상이하며, 서로 독립적으로 단일결합, 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기일 수 있다.In this case, the rest of the W 4 to W 7 other than the phenylene group are the same or different, and each independently a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 1 - It may be a C 12 alkylene group.
또한, 본 발명에서 상기 [화학식 B] 및 [화학식 C]에서의 W4 내지 W7 중에서 3 이상이 치환 또는 비치환된 C6-C30의 아릴렌기인 경우의 구체적인 예로서, 상기 W4 내지 W7 중에서 3개 또는 4개가 치환 또는 비치환된 페닐렌기일 수 있다. 여기서 상기 상기 W4 내지 W7 중 3개가 치환 또는 비치환된 페닐렌기인 경우에 페닐렌기가 아닌 나머지 1개는 단일결합, 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기일 수 있다.In addition, in the present invention, as a specific example when 3 or more of W 4 to W 7 in [Formula B] and [Formula C] are a substituted or unsubstituted C 6 -C 30 arylene group, the W 4 to 3 or 4 of W 7 may be a substituted or unsubstituted phenylene group. Here , when three of W 4 to W 7 are a substituted or unsubstituted phenylene group, the remaining one other than a phenylene group is a single bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted It may be a C 1 -C 12 alkylene group.
또한, 본 발명에서의 상기 [화학식 B] 및 [화학식 C] 내 상기 X4 내지 X7는 동일하거나 상이하며, 서로 독립적으로 O, S, -N(-R22)- , -O((CH2)mO)n- 중에서 선택된 어느 하나일 수 있고, 이때, 상기 m 및 n은 각각 동일하거나 상이하며, 서로 독립적으로 1 내지 4 중에서 선택되는 정수이고, 상기 X4 내지 X7 중 2 이상이 각각 -N(-R22)- 를 선택하거나 또는 상기 X4 내지 X7 중 2 이상이 각각 -O((CH2)mO)n-를 선택하는 경우에 각각의 -N(-R22)- 및 -O((CH2)mO)n-는 각각 동일하거나 상이하며,In addition, in the [Formula B] and [Formula C] in the present invention, X 4 to X 7 are the same or different, and each independently O, S, -N(-R 22 )-, -O((CH 2 ) m O) may be any one selected from n -, wherein m and n are the same or different from each other, and each independently represent an integer selected from 1 to 4, and 2 or more of X 4 to X 7 each -N (-R 22) - or selected or the X 4 to X 7 is 2 or more -O ((CH 2) m O ) of each of the n - each -N (-R 22) when selecting a - and -O((CH 2 ) m O) n - are each the same or different,
상기 R22는 각각 동일하거나 상이하며, 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C50의 아릴기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C7-C24의 아릴알킬기 중에서 선택된 어느 하나일 수 있다.wherein R 22 is the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C3-C30 cyclo It may be any one selected from an alkyl group, a substituted or unsubstituted C7-C24 arylalkyl group.
또한, 본 발명에서의 상기 [화학식 B] 및 [화학식 C]에서 X4 내지 X7 중 적어도 1개는 산소원자(O)일 수 있고, 이 경우 [화학식 B] 및 [화학식 C]로 표시되는 화합물로부터 제조된 감광성 조성물 또는 열경화성 조성물은 가교성 및 기계적 특성이 우수한 특성을 가질 수 있으며, 바람직하게는 X4 내지 X7 중 적어도 2개는 산소원자(O) 일 수 있다.In addition, in the [Formula B] and [Formula C] in the present invention, at least one of X 4 to X 7 may be an oxygen atom (O), and in this case, represented by [Formula B] and [Formula C] The photosensitive composition or thermosetting composition prepared from the compound may have excellent crosslinking properties and mechanical properties, and preferably , at least two of X 4 to X 7 may be an oxygen atom (O).
한편, 본 발명에서의 상기 화학식 A에서와 마찬가지로 상기 X4 내지 X7 중 적어도 하나가 산소원자(-O- )이며, 이와 동시에 상기 산소원자와 결합되는 W4 또는 W5 또는 W6 또는 W7 이 치환 또는 비치환 페닐렌기에 해당하는 경우에, 상기 산소원자는 연결기 L(L4 내지 L7)을 기준으로 오르쏘 또는 메타위치에 결합될 수 있다.On the other hand, as in Formula A in the present invention, at least one of X 4 to X 7 is an oxygen atom (-O- ), and at the same time, W 4 or W 5 or W 6 or W 7 which is bonded to the oxygen atom In the case of the substituted or unsubstituted phenylene group, the oxygen atom may be bonded to the ortho or meta position based on the linking group L (L 4 to L 7 ).
이는 상기 W4 내지 W7 중 적어도 하나이상이 치환 또는 비치환 페닐렌기에 해당하는 경우에 이들에 결합하는 산소원자가 파라위치에 결합하는 경우에, 화학식 A에서 살펴본 바와 마찬가지로, 얻어지는 화합물의 용해도가 낮아져 조성물에서 결정이 석출되는 문제점을 내포하기 때문으로서, 본 발명에서는 상기 산소원자를 연결기 L(L4 내지 L7)을 기준으로 오르쏘 또는 메타위치에 결합된 화합물을 사용하여 이를 해소할 수 있다.This is because when at least one of W 4 to W 7 corresponds to a substituted or unsubstituted phenylene group, when an oxygen atom bonded to them is bonded to the para position, as shown in Formula A, the solubility of the obtained compound is lowered. Since it involves the problem of crystal precipitation in the composition, in the present invention, it can be solved by using a compound in which the oxygen atom is bonded to the ortho or meta position based on the linking group L (L 4 to L 7 ).
즉, 본 발명에서의 상기 [화학식 B] 및 [화학식 C]로 표시되는 화합물은, 상기 X4는 -O- 이고, 상기 W4이 치환 또는 비치환된 페닐렌기이며, 이때, 상기 X4은 L4을 기준으로 오르쏘 또는 메타 위치에 치환되거나; 또는, 상기 X5 는 -O- 이고, 상기 W5이 치환 또는 비치환된 페닐렌기이며, 이때, 상기 X5은 L5을 기준으로 오르쏘 또는 메타 위치에 치환되거나; 또는, 상기 X6 는 -O- 이고, 상기 W6이 치환 또는 비치환된 페닐렌기이며, 이때, 상기 X6은 L5을 기준으로 오르쏘 또는 메타 위치에 치환되거나; 또는, 상기 X7 는 -O- 이고, 상기 W7이 치환 또는 비치환된 페닐렌기이며, 이때, 상기 X7은 L7을 기준으로 오르쏘 또는 메타 위치에 치환되는 화합물을 사용하는 것이 바람직하다.That is, in the compounds represented by [Formula B] and [Formula C] in the present invention, X 4 is -O-, and W 4 is a substituted or unsubstituted phenylene group, in which case, X 4 is Ortho or meta position with respect to L 4 is substituted; Alternatively, X 5 is -O-, and W 5 is a substituted or unsubstituted phenylene group, wherein X 5 is ortho or meta-substituted with respect to L 5 ; Alternatively, X 6 is -O-, and W 6 is a substituted or unsubstituted phenylene group, wherein X 6 is ortho or meta-substituted with respect to L 5 ; Alternatively, X 7 is -O-, and W 7 is a substituted or unsubstituted phenylene group, wherein X 7 is preferably a compound substituted at an ortho or meta position with respect to L 7 . .
또한, 본 발명에서의 상기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물의 구체적인 예로서는 하기 표 1에 기재된 화합물 1 내지 51 중에서 어느 하나로 표시되는 화합물이 될 수 있으나, 이에 제한되지 않는다. In addition, a specific example of the compound represented by any one of [Formula A] to [Formula C] in the present invention may be a compound represented by any one of compounds 1 to 51 described in Table 1 below, but is not limited thereto.
<화합물 1> <화합물 2><Compound 1> <Compound 2>
<화합물 3> <화합물 4><Compound 3> <Compound 4>
<화합물 5> <화합물 6><Compound 5> <Compound 6>
<화합물 7> <화합물 8><Compound 7> <Compound 8>
<화합물 9> <화합물 10><Compound 9> <Compound 10>
<화합물 11> <화합물 12><Compound 11> <Compound 12>
<화합물 13> <화합물 14><Compound 13> <Compound 14>
<화합물 15> <화합물 16><Compound 15> <Compound 16>
<화합물 17> <화합물 18><Compound 17> <Compound 18>
<화합물 19> <화합물 20><Compound 19> <Compound 20>
<화합물 21> <화합물 22><Compound 21> <Compound 22>
<화합물 23> <화합물 24><Compound 23> <Compound 24>
<화합물 25> <화합물 26><Compound 25> <Compound 26>
<화합물 27> <화합물 28><Compound 27> <Compound 28>
<화합물 29> <화합물 30><Compound 29> <Compound 30>
<화합물 31> <화합물 32><Compound 31> <Compound 32>
<화합물 33> <화합물 34><Compound 33> <Compound 34>
<화합물 35> <화합물 36> <Compound 35> <Compound 36>
<화합물 37> <화합물 38><Compound 37> <Compound 38>
<화합물 39> <화합물 40> <Compound 39> <Compound 40>
<화합물 41> <화합물 42><Compound 41> <Compound 42>
<화합물 43> <화합물 44><Compound 43> <Compound 44>
<화합물 45> <화합물 46> <Compound 45> <Compound 46>
<화합물 47> <화합물 48><Compound 47> <Compound 48>
<화합물 49> <화합물 50><Compound 49> <Compound 50>
<화합물 51><Compound 51>
본 발명은 트리아진 고리를 가지는 화합물로서, 분자 말단에 에폭시기를 포함하는 광경화성 또는 열경화성 모노머 화합물을 기술적 특징으로 한다. 즉, 종래의 트리아진 화합물은 굴절율이 높은 특성임에도 불구하고, 트리아진 유도체의 분자 구조내에 중합에 사용되는 에폭시기의 개시제 특성을 갖는 '-NH-'기를 포함하고 있는 경우에 트리아진 고리를 포함하는 분자내에 에폭시기를 도입하기 어려웠으나, 본 발명에서는 반응물인 에폭시기 화합물(e.g.에피클로히드린) 및 강염기의 당량을 적절히 조절하여 높은 수율로 상기 [화학식 A] 내지 [화학식 C]중 어느 하나로 표시되는 화합물을 합성할 수 있다.The present invention is a compound having a triazine ring, and a photocurable or thermosetting monomer compound including an epoxy group at the molecular terminal is a technical feature. That is, when the conventional triazine compound contains a '-NH-' group having an initiator characteristic of an epoxy group used for polymerization in the molecular structure of the triazine derivative, despite the characteristic of a high refractive index, it contains a triazine ring. Although it was difficult to introduce an epoxy group into the molecule, in the present invention, the compound represented by any one of the above [Formula A] to [Formula C] in high yield by appropriately adjusting the equivalent of the reactant epoxy group compound (eg epichlorohydrin) and a strong base can be synthesized.
아래의 반응식 1 은 본 발명에 따른 트리아진 화합물내 에폭시기를 도입하기 위한 합성 메커니즘의 일부를 나타낸 것이며, 적절히 치환기를 변경하여 상기 [화학식 A], [화학식 B] 및 [화학식 C] 중 어느 하나로 표시되는 다양한 에폭시기를 포함하는 화합물을 합성할 수 있다.Scheme 1 below shows a part of the synthesis mechanism for introducing an epoxy group in the triazine compound according to the present invention, and by changing the substituent appropriately, it is represented by any one of [Formula A], [Formula B] and [Formula C] Compounds containing various epoxy groups can be synthesized.
[반응식 1] [Scheme 1]
이때, 본 발명에 따른 [화학식 A] 내지 [화학식 C]중 어느 하나로 표시되는 화합물을 합성하기 위한 반응물로서 사용되는 에폭시기 화합물은 에피클로로히드린, 2-(클로로메틸)-1,2-에폭시프로판, 2-(클로로메틸)-1,2-에폭시부탄 중에서 선택되는 어느 하나를 사용할 수 있으며, 이의 사용함량은 트리아진 화합물에 대하여 대하여 3 ~ 100 당량의 범위, 바람직하게는 10 ~ 50 당량의 범위로 첨가할 수 있고, 또한 강염기는 트리아진 화합물에 대하여 0.5 ~ 10 당량, 바람직하게는 0.5 ~ 2 당량의 범위로 첨가할 수 있다.At this time, the epoxy group compound used as a reactant for synthesizing the compound represented by any one of [Formula A] to [Formula C] according to the present invention is epichlorohydrin, 2-(chloromethyl)-1,2-epoxypropane , 2-(chloromethyl)-1,2-epoxybutane may be used, and the content thereof is in the range of 3 to 100 equivalents, preferably in the range of 10 to 50 equivalents, based on the triazine compound. In addition, the strong base may be added in the range of 0.5 to 10 equivalents, preferably 0.5 to 2 equivalents, based on the triazine compound.
또한, 반응 압력은 0.5 기압 내지 2기압의 범위에서, 반응온도는 섭씨 0 내지 100 도의 조건하에서 반응이 이루어질 수 있다. In addition, the reaction pressure may be in the range of 0.5 atm to 2 atm, and the reaction may be carried out under conditions of 0 to 100 degrees Celsius at the reaction temperature.
이러한 반응 조건에 따라 합성을 진행함으로써, 본 발명에 따른 [화학식 A] 내지 [화학식 C]중 어느 하나로 표시되는 화합물을 높은 수율로 제조할 수 있다.By performing the synthesis according to these reaction conditions, the compound represented by any one of [Formula A] to [Formula C] according to the present invention can be prepared in high yield.
한편, 본 발명은 상기 [화학식 A] 내지 [화학식 C]중 어느 하나로 표시되는 화합물을 포함하는 감광성 조성물 또는 열가교성 조성물을 제공한다.On the other hand, the present invention provides a photosensitive composition or a thermally crosslinkable composition comprising a compound represented by any one of the above [Formula A] to [Formula C].
즉, 본 발명에 따른 상기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물은 광산발생제가 포함되어 있는 조성물을 제조하여 감광성 조성물을 제조하거나, 또는 열산발생제를 포함하는 조성물을 제조하여 열가교성 조성물을 제조할 수 있다. That is, the compound represented by any one of [Formula A] to [Formula C] according to the present invention is prepared by preparing a composition containing a photoacid generator to prepare a photosensitive composition, or by preparing a composition containing a thermal acid generator A thermally crosslinkable composition can be prepared.
특히, 본 발명에 따른 상기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물은 감광성 조성물 내에서 광가교성 모노머로서 포함되어 UV 등과 같은 광에 의해 박막 또는 프리즘 등을 형성할 수 있고, 상기 감광성 조성물을 디스플레이용이나 전자재료용 조성물에 사용하는 경우에 용매나 에폭시, 에폭시아크릴 모노머와의 상용성이 우수한 효과가 있다.In particular, the compound represented by any one of [Formula A] to [Formula C] according to the present invention is included as a photo-crosslinkable monomer in the photosensitive composition to form a thin film or a prism by light such as UV, etc., When the photosensitive composition is used for a display or a composition for an electronic material, there is an effect excellent in compatibility with a solvent, an epoxy, or an epoxy acryl monomer.
또한, 상기 [화학식 A] 내지 [화학식 C]중 어느 하나로 표시되는 화합물은 굴절율, 투과도 및 내황변 특성이 우수하여 TFT-LCD용 및 OLED용 고굴절 모노머로 사용시 휘도 및 성능을 향상시킬 수 있다.In addition, the compound represented by any one of [Formula A] to [Formula C] has excellent refractive index, transmittance, and yellowing resistance properties, so that when used as a high refractive monomer for TFT-LCD and OLED, luminance and performance can be improved.
이를 위해서 상기 조성물은 광개시제, 열개시제, 광중합성 모노머, 열중합성 모노머를 추가적으로 포함할 수 있으며, 이에 제한되지 않고 기타 공지의 감광성 조성물에 사용되는 물질을 추가적으로 포함할 수 있다.To this end, the composition may additionally include a photoinitiator, a thermal initiator, a photopolymerizable monomer, and a thermally polymerizable monomer, but is not limited thereto, and may additionally include a material used in other known photosensitive compositions.
또한, 본 발명은 상기 감광성 조성물을 중합하여 얻어지는 광학 소재를 제공한다.In addition, the present invention provides an optical material obtained by polymerizing the photosensitive composition.
또한, 본 발명의 상기 감광성 조성물의 일 실시예로서, 조성물 100 중량부에 대해서, 상기 [화학식 A] 내지 [화학식 C] 중 어느 하나로 표시되는 화합물 1 내지 95 중량부, 광중합성 모노머 0 내지 90 중량부 및 광개시제 0.1 내지 20 중량부를 포함할 수 있다.In addition, as an embodiment of the photosensitive composition of the present invention, with respect to 100 parts by weight of the composition, 1 to 95 parts by weight of a compound represented by any one of [Formula A] to [Formula C], 0 to 90 parts by weight of a photopolymerizable monomer parts and 0.1 to 20 parts by weight of a photoinitiator.
여기서, 상기 광중합 모노머 또는 열중합성 모노머는 방향족 고리와 지방족 고리의 양방을 갖는 페놀 화합물과 에피할로히드린의 축합중합; 방향족, 지방족고리, 또는 그 양방을 갖는 에폭시 수지와 방향족 고리, 지방족고리 또는 그 양방을 갖는 페놀 화합물의 부가중합; 방향족 고리, 지방족고리 또는 그 양방을 갖는 산 무수물과 방향족고리 , 지방족고리 또는 그 양방을 갖는 에폭시 수지의 부가중합; 방향족고리, 지방족 고리, 또는 그 양방을 갖는 말단 카르복실기의 에스테르 화합물과 방향족고리 지방족고리 또는 그 양방을 갖는 에폭시 수지의 부가 중합 등 에 사용될 수 있다.Here, the photopolymerizable monomer or the thermally polymerizable monomer is a phenolic compound having both an aromatic ring and an aliphatic ring, and a condensation polymerization of epihalohydrin; addition polymerization of an epoxy resin having an aromatic ring, an aliphatic ring, or both, and a phenol compound having an aromatic ring, an aliphatic ring, or both; addition polymerization of an acid anhydride having an aromatic ring, an aliphatic ring or both, and an epoxy resin having an aromatic ring, an aliphatic ring, or both; It can be used for addition polymerization of an ester compound of a terminal carboxyl group having an aromatic ring, an aliphatic ring, or both, and an epoxy resin having an aromatic ring, an aliphatic ring, or both.
여기서 방향족 고리를 갖는 에폭시 수지로는, 2관능 페놀 화합물은 글리시디에테르화물인 2관능 방향족 에폭시 수지이고, 2관능 페놀 화합물로는 비스페놀A, 비스페놀F, 비스페놀S, 4,4'-비페놀, 테트라메틸비스페닐A, 디메틸비스페놀A, 테트라메틸비스페놀F, 디메틸비스페놀F, 테트라메틸비스페놀S, 디메티리스페놀S, 테트라메틸-4,4'-비페놀, 디메틸-4,4'-비페놀 1-(4-하이드록시페닐)-2-[4-(1,1-비스-(4-하이드록시페닐)에틸)페닐]프로판, 2,2'-메틸렌-비스(4-메틸-6-tert-부틸페놀), 4,4'-부틸리덴-비스(3-메틸-6-tert-부틸페놀), 트리스하이드록시페닐메탄, 레조르시놀, 하이드로퀴논, 9,9-비스(4-하이드록시페닐)-9H-플루오렌, 9,9-비스(4-하이드록시-3-메틸페닐)-9H-플루오렌 등의 2 관능 방향족 페놀을 들 수 있고, 단독 또는 2 종 이상의 혼합물로서 사용할 수 있지만, 이들에 한정되는 것은 아니다. Here, as the epoxy resin having an aromatic ring, the bifunctional phenol compound is a bifunctional aromatic epoxy resin that is a glycidieteride, and as the bifunctional phenol compound, bisphenol A, bisphenol F, bisphenol S, 4,4'-biphenol, Tetramethylbisphenyl A, dimethylbisphenol A, tetramethylbisphenol F, dimethylbisphenol F, tetramethylbisphenol S, dimethyrisphenol S, tetramethyl-4,4'-biphenol, dimethyl-4,4'-biphenol 1-(4-hydroxyphenyl)-2-[4-(1,1-bis-(4-hydroxyphenyl)ethyl)phenyl]propane, 2,2'-methylene-bis(4-methyl-6- tert-butylphenol), 4,4'-butylidene-bis(3-methyl-6-tert-butylphenol), trishydroxyphenylmethane, resorcinol, hydroquinone, 9,9-bis(4- and bifunctional aromatic phenols such as hydroxyphenyl)-9H-fluorene and 9,9-bis(4-hydroxy-3-methylphenyl)-9H-fluorene, and may be used alone or as a mixture of two or more types. However, it is not limited to these.
상기 방향족 고리를 갖는 산 무수물로는, 무수프탈산, 1,2-나프탈렌디카르복실산 무수물, 2,3-나프탈렌디카르복실산무수물, 1,2,3,4-테트라하이드로-1,2-나프탈렌디카르복실산 무수물 등을 들 수 있고, 단독 또는 2 종 이상의 혼합물로서 사용할 수 있지만, 이들에 한정되는 것은 아니다.Examples of the acid anhydride having an aromatic ring include phthalic anhydride, 1,2-naphthalenedicarboxylic acid anhydride, 2,3-naphthalenedicarboxylic acid anhydride, 1,2,3,4-tetrahydro-1,2- Naphthalenedicarboxylic acid anhydride etc. are mentioned, Although it can use individually or as a mixture of 2 or more types, it is not limited to these.
또한, 일예로서, 상기 광중합 모노머 또는 열중합성 모노머는 방향족 고리를 갖는 디카르복실산이 사용될 수 있으며, 방향족 고리를 갖는 디카르복실산의 구체적인 예로서는, 프탈산, 1,2-나프탈렌디카르복실산, 2,3-나프탈렌디카르복실산, 1,2,3,4-테트라하이드로나프탈렌-2,3-디카르복실산, 1-페닐-2,6-나프탈렌디카르복실산 등을 들 수 있고, 단독또는 2 종 이상의 혼합물로서 사용할 수 있지만, 이들에 한정되는 것은 아니다.In addition, as an example, the photopolymerizable monomer or the thermally polymerizable monomer may be dicarboxylic acid having an aromatic ring, and specific examples of the dicarboxylic acid having an aromatic ring include phthalic acid, 1,2-naphthalenedicarboxylic acid, 2 , 3-naphthalenedicarboxylic acid, 1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid, 1-phenyl-2,6-naphthalenedicarboxylic acid, etc. are mentioned, and single Or it can be used as a mixture of 2 or more types, but is not limited to these.
한편, 상기 감광성 조성물은 중합성 수지(페놀계 수지, 노볼락형 수지)를 추가적으로 포함할 수 있으며, 상기 페놀계 수지로서는 페놀노볼락수지, 그레졸 노볼락수지등이 사용될 수 있다.Meanwhile, the photosensitive composition may additionally include a polymerizable resin (phenol-based resin, novolak-type resin), and as the phenol-based resin, a phenol novolak resin, a gresol novolak resin, or the like may be used.
상기 광개제는 광산발생제로써 다음과 같은 예를 들 수 있다. 요오드늄염으로서, 예를 들어 디페닐요오드늄클로라이드, 디페닐요오드늄트리플루오로메탄술포네이트, 디페닐요오드늄메실레이트, 디페닐요오드늄토실레이트, 디페닐요오드늄브로마이드, 디페닐요오드늄테트라플루오로보레이트, 디페닐요오드늄헥사플루오로안티모네이트, 디페닐요오드늄헥사플루, 오로아르세네이트, 비스(p-tert-부틸페닐)요오드늄헥사플루오로포스페이트, 비스(p-tert-부틸페닐)요오드늄메실레이트, 비스(p-tert-부틸페닐)요오드늄토실레이트, 비스(p-tert-부틸페닐)요오드늄트리플루오로메탄술포네이트, 비스(p-tert-부틸페닐)요오드늄테트라플루오로보레이트, 비스(p-tert-부틸페닐)요오드늄클로라이드, 비스(p-클로로페닐)요오드늄클로라이드, 비스(p-클로로페닐)요오드늄테트라플루오로보레이트를 들 수 있다. 또한 비스(4-t-부틸페닐)요오드늄헥사플루오로포스페이트 등의비스(알킬페닐)요오드늄염, 알콕시카르보닐알콕시-트리알킬아릴요오드늄염(예를 들어, 4-[(1-에톡시카르보닐-에톡시)페닐]-(2,4,6-트리메틸페닐)-요오드늄헥사플루오로포스페이트 등), 비스(알콕시아릴)요오드늄염(예를들어, (4-메톡시페닐)페닐요오드늄헥사플루오로안티모네이트 등의 비스(알콕시페닐)요오드늄염), 트리페닐술포늄클로라이드, 트리페닐술포늄브로마이드, 트리(p-메톡시페닐)술포늄테트라플루오로보레이트, 트리(p-메톡시페닐)술포늄헥사플루오로포스포네이트, 트리(p-에톡시페닐)술포늄테트라플루오로보레이트, 트리페닐술포늄트리플레이트, 트리페닐술포늄헥사플루오로안티모네이트, 트리페닐술포늄헥사플루오로포스페이트, 트리페닐술포늄노나플루오르부탄설포네이트등의 트리페닐술포늄염이나, (4-페닐티오페닐)디페닐술포늄헥사플루오로안티모네이트, (4-페닐티오페닐)디페닐술포늄헥사플루오로포스페이트, 비스[4-(디페닐술포니오)페닐]설파이드-비스-헥사플루오로안티모네이트, 비스[4-(디페닐술포니오)페닐]설파이드-비스-헥사플루오로포스페이트, (4-메톡시페닐)디페닐술포늄헥사플루오로안티모네이트), 트리페닐포스포늄클로라이드, 트리페닐포스포늄브로마이드, 트리(p-메톡시페닐)포스포늄 테트라플루오로보레이트, 트리(p-메톡시페닐)포스포늄 헥사플루오로포스포네이트, 트리(p-에톡시페닐)포스포늄 테트라플루오로보레이트, 4-클로로벤젠디아조늄 헥사플루오로포스페이트, 질트리페닐포스포늄 헥사플루오로안티모네이트, 트리페닐셀레늄 헥사플루오로포스페이트 등의 셀레늄염이, 또한 메탈로센 착체로 (η5 또는 η6-이소프로필벤젠)(η5-시클로펜타디에닐)철(II)헥사플루오로포스페이트 등을 들 수 있으나 이를 한정하는 것은 아니다. 이러한 광개시제는 보다 바람직하게는, 노광 감도와 패턴 특성을 조절하기 위하여 감광성 조성물 100중량부를 기준으로 0.1 내지 20중량부를 사용할 수 있다.The photoinitiator may be exemplified as a photoacid generator as follows. As the iodonium salt, for example, diphenyl iodonium chloride, diphenyl iodonium trifluoromethanesulfonate, diphenyl iodonium mesylate, diphenyl iodonium tosylate, diphenyl iodonium bromide, diphenyl iodonium tetrafluoro Roborate, diphenyliodonium hexafluoroantimonate, diphenyliodonium hexaflu, oroarsenate, bis(p-tert-butylphenyl)iodonium hexafluorophosphate, bis(p-tert-butylphenyl) ) iodonium mesylate, bis(p-tert-butylphenyl)iodonium tosylate, bis(p-tert-butylphenyl)iodonium trifluoromethanesulfonate, bis(p-tert-butylphenyl)iodoniumtetra and fluoroborate, bis(p-tert-butylphenyl)iodonium chloride, bis(p-chlorophenyl)iodonium chloride, and bis(p-chlorophenyl)iodoniumtetrafluoroborate. In addition, bis(alkylphenyl)iodonium salts such as bis(4-t-butylphenyl)iodonium hexafluorophosphate, alkoxycarbonylalkoxy-trialkylaryliodonium salts (e.g., 4-[(1-ethoxycar Bornyl-ethoxy)phenyl]-(2,4,6-trimethylphenyl)-iodonium hexafluorophosphate, etc.), bis(alkoxyaryl)iodonium salt (e.g., (4-methoxyphenyl)phenyliodonium Bis(alkoxyphenyl)iodonium salt such as hexafluoroantimonate), triphenylsulfonium chloride, triphenylsulfonium bromide, tri(p-methoxyphenyl)sulfonium tetrafluoroborate, tri(p-methoxy Phenyl) sulfonium hexafluorophosphonate, tri (p-ethoxyphenyl) sulfonium tetrafluoroborate, triphenyl sulfonium triflate, triphenyl sulfonium hexafluoroantimonate, triphenyl sulfonium hexafluoro Triphenylsulfonium salts such as lophosphate and triphenylsulfonium nonafluorobutanesulfonate, (4-phenylthiophenyl)diphenylsulfonium hexafluoroantimonate, (4-phenylthiophenyl)diphenylsulfoniumhexa fluorophosphate, bis[4-(diphenylsulfonio)phenyl]sulfide-bis-hexafluoroantimonate, bis[4-(diphenylsulfonio)phenyl]sulfide-bis-hexafluorophosphate, (4-methoxyphenyl) diphenylsulfonium hexafluoroantimonate), triphenylphosphonium chloride, triphenylphosphonium bromide, tri (p-methoxyphenyl) phosphonium tetrafluoroborate, tri (p- Methoxyphenyl) phosphonium hexafluorophosphonate, tri (p-ethoxyphenyl) phosphonium tetrafluoroborate, 4-chlorobenzenediazonium hexafluorophosphate, nitrogen triphenylphosphonium hexafluoroantimonate and selenium salts such as triphenyl selenium hexafluorophosphate, and metallocene complexes such as (η5 or η6-isopropylbenzene)(η5-cyclopentadienyl)iron(II)hexafluorophosphate. This is not limiting. More preferably, 0.1 to 20 parts by weight of the photoinitiator may be used based on 100 parts by weight of the photosensitive composition in order to control exposure sensitivity and pattern characteristics.
또한, 상기 감광성 조성물을 용해하는데 선택적으로 유기용매가 사용될 수 있으며, 점도 조절과 코팅 특성 개선을 위해 사용되며, 이러한 용매로는 유기용매를 사용하는 것이 바람직하다.In addition, an organic solvent may optionally be used to dissolve the photosensitive composition, and the viscosity control and It is used to improve coating properties, and it is preferable to use an organic solvent as such a solvent.
상기 유기용매로서, 바람직하게는 테트라하이드로퓨란, 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르, 메틸셀로솔브아세테이트, 에틸셀로솔브아세테이트, 디에틸렌글리콜모노메틸에테르, 디에틸렌글리콜모노에틸에테르, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 디에틸렌글리콜에틸메틸에테르, 프로필렌글리콜메틸에테르, 프로필렌글리콜에틸에테르, 프로필렌글리콜프로필에테르, 프로필렌글리콜부틸에테르, 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜에틸에테르아세테이트, 프로필렌글리콜프로필에테르아세테이트, 프로필렌글리콜부틸에테르아세테이트, 프로필렌글리콜메틸에테르프로피오네이트, 프로필렌글리콜에틸에테르프로피오네이트, 프로필렌글리콜프로필에테르프로피오As the organic solvent, preferably tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether Acetate, propylene glycol propyl ether acetate, propylene glycol butyl ether acetate, propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate, propylene glycol propyl ether propio
네이트, 프로필렌글리콜부틸에테르프로피오네이트, 톨루엔, 자일렌, 메틸에틸케톤, 시클로헥사논, 4-하이드록시-4-메틸-2-펜타논 아세트산메틸, 아세트산에틸, 아세트산프로필, 아세트산부틸, 2-이드록시프로피온산에틸, 2-하이드록시-2-메틸프로피온산메틸, 2-하이드록시-2-메틸프로피온산에틸, 하이드록시아세트산메틸, 하이드록시아세트산에틸, 하이드록시아세트산부틸, 유산메틸, 유산에틸, 유산프로필, 유산부틸, 3-하이드록시프로피온산메틸, 3-하이드록시프로피온산에틸, 3-하이드록시프로피온산프로필, 3-하이드록시프로피온산부틸, 2-하이드록시-3-메틸부탄산메틸, 메톡시아세트산메틸, 메톡시아세트산에틸, 메톡시아세트산프로필, 메톡시아세트산부틸, 에톡시아세트산메틸, 에톡시아세트산에틸, 에톡시아세트산프로필, 에톡시아세트산부틸, 프로폭시아세트산메틸, 프로폭시아세트산에틸, 프로폭시아세트산프로필, 프로폭시아세트산부틸, 부톡시아세트산메틸, 부톡시아세트산에틸, 부톡시아세트산프로필, 부톡시아세트산부틸, 2-메톡시프로피온산메틸, 2-메톡시프로피온산에틸, 2-메톡시프로피온산프로필, 2-메톡시프로피온산부틸, 2-에톡시프로피온산메틸, 2-에톡시프로피온산에틸, 2-에톡시프로피온산프로필, 2-에톡시프로피온산부틸, 2-부톡시프로피온산메틸, 2-부톡시프로피온산에틸, 2-부톡시프로피온산프로필,2-부톡시프로피온산부틸, 3-메톡시프로피온산메틸, 3-메톡시프로피온산에틸, 3-메톡시프로피온산프로필, 3-메톡시프로피온산부틸, 3-에톡시프로피온산메틸, 3-에톡시프로피온산에틸, 3-에톡시프로피온산프로필, 3-에톡시프로피온산부틸, 3-프로폭시프로피온산메틸, 3-프로폭시프로피온산에틸, 3-프로폭시프로피온산프로필, 3-프로폭시프로피온산부틸, 3-부톡시프로피온산메틸, 3-부톡시프로피온산에틸, 3-부톡시프로피온산프로필, 3-부톡시프로피온산부틸 헥산, 헵탄 및 옥탄 등을 들수 있으며 이를 한정하는 것은 아니다. 또한 위 용매에서 선택된 1종 이상을 사용할 수 있으며, 여기서 상기 용매의 함량은 상기 감광성 조성물 100 중량부를 기준으로 0 내지 90 중량부를 포함하는 것이 바람직하다.Nate, propylene glycol butyl ether propionate, toluene, xylene, methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone methyl acetate, ethyl acetate, propyl acetate, butyl acetate, 2- Ethyl hydroxypropionate, 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl hydroxyacetate, ethyl hydroxyacetate, butyl hydroxyacetate, methyl lactate, ethyl lactate, propyl lactate , butyl lactate, 3-hydroxymethyl propionate, 3-hydroxyethyl propionate, 3-hydroxypropionate propyl, 3-hydroxypropionate butyl, 2-hydroxy-3-methyl butanoate, methyl methoxyacetate, Ethyl oxyacetate, propyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, ethyl ethoxy acetate, propyl ethoxy acetate, butyl ethoxy acetate, methyl propoxy acetate, ethyl propoxy acetate, propyl propoxy acetate, propoxy acetate Butyl acetate, methyl butoxy acetate, ethyl butoxy acetate, propyl butoxy acetate, butyl butoxy acetate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, 2-methoxypropionic acid Butyl, 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-ethoxypropionate propyl, 2-ethoxypropionate butyl, 2-butoxypropionate methyl, 2-butoxypropionate ethyl, 2-butoxypropionate propyl , 2-Butoxy butyl propionate, 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-methoxy propyl propionate, 3-methoxy butyl propionate, 3-ethoxy methyl propionate, 3-ethoxy propionate ethyl, 3-ethoxypropionate propyl, 3-ethoxypropionate butyl, 3-propoxypropionate methyl, 3-propoxypropionate ethyl, 3-propoxypropionate propyl, 3-propoxypropionate butyl, 3-butoxypropionate methyl, 3 -ethyl butoxypropionate, 3-butoxypropionate propyl, 3-butoxypropionate butyl hexane, heptane and octane, and the like, but are not limited thereto. In addition, one or more selected from the above solvents may be used, wherein the amount of the solvent is preferably 0 to 90 parts by weight based on 100 parts by weight of the photosensitive composition.
또한, 본 발명에 따른 감광성 조성물 또는 열경화성 조성물은 프리즘시트, 마이크로렌즈, DBEF 필름, LCD용 코팅 재료, 유기발광소자(OLED)용 코팅 재료, 광학렌즈, 다초점렌즈 중에서 선택되는 어느 하나를 제조하기 위해 사용될 수 있다. In addition, the photosensitive composition or thermosetting composition according to the present invention is a prism sheet, a microlens, a DBEF film, a coating material for LCD, a coating material for an organic light emitting device (OLED), an optical lens, any one selected from a multifocal lens To manufacture can be used for
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않는다는 것은 당업계의 통상의 지식을 가진 자에게 자명할 것이다. Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereby.
상기 [화학식 A], [화학식 B] 및 [화학식 C] 중 어느 하나로 표시되는 아크릴기를 포함하는 화합물을 합성하는 대표적인 방법에 대하여 예시하면, 하기 반응식 4와 같다. A representative method for synthesizing a compound containing an acryl group represented by any one of [Formula A], [Formula B] and [Formula C] is illustrated in Reaction Scheme 4 below.
[반응식 4] [Scheme 4]
상기 반응식 4는 상기 에폭시기를 포함하는 화합물 중 일부에 대한 합성 메커니즘을 나타낸 것이며, 적절히 치환기를 변경하여 상기 [화학식 A], [화학식 B] 및 [화학식 C] 중 어느 하나로 표시되는 다양한 에폭시기를 포함하는 화합물을 합성할 수 있다.Scheme 4 shows the synthesis mechanism for some of the compounds containing the epoxy group, and by changing the substituent appropriately, the [Formula A], [Formula B] and [Formula C] containing various epoxy groups represented by any one of compounds can be synthesized.
합성예 1: 화합물 1의 제조Synthesis Example 1: Preparation of Compound 1
합성예 1-1 : 3,3',3''-((1,3,5-트리아진-2,4,6-트라이일리)트리스(아자니디닐)) 트리페놀의 제조Synthesis Example 1-1: Preparation of 3,3',3''-((1,3,5-triazine-2,4,6-trily)tris(azanidinyl))triphenol
1L 3구 플라스크에 THF 300 ml를 넣고 질소분위기 하에 2,4,6-트리클로로-1,3,5-트리아진 20.0 g(108.5 mmol)을 가한다. 반응플라스크를 0 oC로 냉각한 뒤 3-아미노페놀 35.5 g(325.4 mmol)을 교반하면서 30분 동안 천천히 가한 후 쇼듐아세테이트 20.0 g(244.0mmol)을 가한다. 반응용기를 80oC로 가열하여 10시간 동안 교반한다. 반응종료 후 증류수 300ml를 첨가하고 교반하여 흰색 고체 3,3',3''-((1,3,5-triazine-2,4,6-triyl)tris(azanediyl))triphenol 40.1g (수율 92%)을 제조하였다.Put 300 ml of THF in a 1L three-necked flask, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 o C, 35.5 g (325.4 mmol) of 3-aminophenol was slowly added while stirring for 30 minutes, and then 20.0 g (244.0 mmol) of shodium acetate was added. The reaction vessel is heated to 80 o C and stirred for 10 hours. After completion of the reaction, 300 ml of distilled water was added and stirred to 40.1 g of white solid 3,3',3''-((1,3,5-triazine-2,4,6-triyl)tris(azanediyl))triphenol (yield 92) %) was prepared.
합성예 1-2 : 화합물 1의 제조Synthesis Example 1-2: Preparation of compound 1
250ml 3구 플라스크에 이소프로필알콜 100mL, 3,3',3''-((1,3,5-트리아진-2,4,6-트라이일리)트리스(아자니디닐))트리페놀 10.0 g (24.9 mmol), 2-(클로로메틸)옥시란 69.0g(745.5mmol)을 투입하고 70oC로 가열교반하여 용해시킨 후 쇼듐히드록시드 1.0g(24.9mmol)을 적가하고 1시간동안 가열교반한다. 반응이 종결되면 회전식증발기로 용매를 제거한 뒤 에틸아세테이트로 용해하고 과포화소금물로 2~3회 세척하고 무수황산마그네슘으로 건조하고 에틸아세테이트 : 헥산 = 1 : 3으로 컬럼 정제하여 [화합물 1] 12.1 g (수율 81%)을 제조하였다.In a 250ml 3-neck flask, 100mL of isopropyl alcohol, 10.0 g of 3,3',3''-((1,3,5-triazine-2,4,6-trily)tris(azanidinyl))triphenol ( 24.9 mmol) and 2-(chloromethyl)oxirane 69.0 g (745.5 mmol) were added and dissolved by heating at 70 o C. Then, 1.0 g (24.9 mmol) of shodium hydroxide was added dropwise and stirred for 1 hour. . When the reaction is complete, the solvent is removed with a rotary evaporator, dissolved with ethyl acetate, washed with supersaturated brine 2-3 times, dried over anhydrous magnesium sulfate, and column purified with ethyl acetate: hexane = 1: 3 to 12.1 g of [Compound 1] ( Yield 81%) was prepared.
합성예 2: 화합물 3의 제조Synthesis Example 2: Preparation of compound 3
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 3,3',3''-((1,3,5-트리아진-2,4,6-트라이일리)트리스(아자니디닐))트리페놀 10.0 g (24.9 mmol), 2-(클로로메틸)옥시란 23.0g(248.5mmol)을 사용하여 [화합물 3] 8.20g(수율 72%)을 제조하였다.Synthesis Example 1-2 In the same manner as in the preparation of Compound 1, 100 mL of isopropyl alcohol, 3,3',3''-((1,3,5-triazine-2,4,6-triilli)tris(Ajani) [Compound 3] 8.20 g (yield 72%) was prepared using 10.0 g (24.9 mmol) of dinyl)) triphenol and 23.0 g (248.5 mmol) of 2-(chloromethyl) oxirane.
합성예 3: 화합물 5의 제조Synthesis Example 3: Preparation of compound 5
합성예 3-1: 3-((4,6-비스(페닐아미노)-1,3,5-트리아진-2-닐)아미노)페놀의 제조Synthesis Example 3-1: Preparation of 3-((4,6-bis(phenylamino)-1,3,5-triazin-2-yl)amino)phenol
1L 3구 플라스크에 THF 300 ml를 넣고 질소분위기 하에 2,4,6-트리클로로-1,3,5-트리아진 20.0 g(108.5 mmol)을 가한다. 반응플라스크를 0oC로 냉각한 뒤 아닐린 20.2 g(217.0 mmol)을 교반하면서 30분 동안 천천히 가한 후 3시간동안 상온교반한다 3-아미노페놀 11.8 g(108.5 mmol)을 천천히 가한후 쇼듐아세테이트 20.0 g(244.0mmol)을 가한다. 반응용기를 80oC로 가열하여 10시간 동안 교반한다. 반응종료 후 증류수 300ml를 첨가하고 교반하여 흰색 고체 3,3',3''-((1,3,5-트리아진-2,4,6- 트라이일리)트리스(아자니디닐))트리페놀 28.1g (수율 70%)을 제조하였다.Put 300 ml of THF in a 1L three-necked flask, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 o C, 20.2 g (217.0 mmol) of aniline was slowly added with stirring for 30 minutes, followed by stirring at room temperature for 3 hours. After slowly adding 11.8 g (108.5 mmol) of 3-aminophenol, 20.0 g of shodium acetate (244.0 mmol) is added. The reaction vessel is heated to 80 o C and stirred for 10 hours. After completion of the reaction, 300 ml of distilled water was added and stirred, white solid 3,3',3''-((1,3,5-triazine-2,4,6-triyl)tris(azanidinyl))triphenol 28.1 g (yield 70%) was prepared.
합성예 3-2. 화합물 5의 제조Synthesis Example 3-2. Preparation of compound 5
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 3-((4,6-비스(페닐아미노)-1,3,5-트리아진-2-닐)아미노)페놀 10.0 g (27.0 mmol), 2-(클로로메틸)옥시란 25.0g(270.0mmol)을 사용하여 [화합물 5] 10.6g(수율 92%)을 제조하였다.Synthesis Example 1-2 100 mL of isopropyl alcohol, 10.0 g of 3 -((4,6-bis(phenylamino)-1,3,5-triazin-2-yl)amino)phenol in the same manner as in the preparation of compound 1 (27.0 mmol), 25.0 g (270.0 mmol) of 2-(chloromethyl)oxirane was used to prepare 10.6 g (yield 92%) of [Compound 5].
합성예 4: 화합물 13의 제조Synthesis Example 4: Preparation of compound 13
합성예 4-1: 3,3'-((6-(페닐티오)-1,3,5-트리아진-2,4-디닐)비스(아자니Synthesis Example 4-1: 3,3'-((6-(phenylthio)-1,3,5-triazine-2,4-dinyl)bis(azani)
디닐))디페놀의 제조dinyl)) production of diphenol
합성예 3-1 과 동일한 방법으로 2,4,6-트리클로로-1,3,5-트리아진 20.0 g(108.5 mmol) 3-아미노페놀 23.7 g(217.0 mmol), 티오페놀12.0 g(108.5 mmol), 쇼듐아세테이트 20.0 g(244.0mmol)을 사용하여 흰색 고체 3,3'-((6-(페닐티오)-1,3,5-트리아진-2,4-디닐)비스(아자니디닐))디페놀 31.9g (수율 73%)을 제조하였다.In the same manner as in Synthesis Example 3-1, 2,4,6-trichloro-1,3,5-triazine 20.0 g (108.5 mmol) 3-aminophenol 23.7 g (217.0 mmol), thiophenol 12.0 g (108.5 mmol) ), using 20.0 g (244.0 mmol) of shodium acetate as a white solid 3,3'-((6-(phenylthio)-1,3,5-triazine-2,4-dinyl)bis(azanidinyl)) 31.9 g of diphenol (yield 73%) was prepared.
합성예 4-2: 화합물 13의 제조Synthesis Example 4-2: Preparation of compound 13
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 3,3'-((6-(페닐티오)-1,3,5-트리아진-2,4-디닐)비스(아자니디닐))디페놀 10.0 g (24.8 mmol), 2-(클로로메틸)옥시란 45.9g(495.7mmol)을 사용하여 [화합물 13] 11.5g(수율 90%)을 제조하였다.Synthesis Example 1-2 In the same manner as in the preparation of Compound 1, 100 mL of isopropyl alcohol, 3,3'-((6-(phenylthio)-1,3,5-triazine-2,4-dinyl)bis(Ajani) denyl)) diphenol 11.5 g (yield 90%) of [Compound 13] was prepared using 10.0 g (24.8 mmol) and 45.9 g (495.7 mmol) of 2-(chloromethyl)oxirane.
합성예 5: 화합물 21의 제조Synthesis Example 5: Preparation of compound 21
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 3-((4,6-비스(페닐아미노)-1,3,5-트리아진-2-닐)아미노)페놀 10.0 g (27.0 mmol), 2-(클로로메틸)-2-메틸옥시란 28.8g(270.0mmol)을 사용하여 [화합물 21] 10.2g(수율 86%)을 제조하였다.Synthesis Example 1-2 100 mL of isopropyl alcohol, 10.0 g of 3 -((4,6-bis(phenylamino)-1,3,5-triazin-2-yl)amino)phenol in the same manner as in the preparation of compound 1 (27.0 mmol), 2-(chloromethyl)-2-methyloxirane 28.8 g (270.0 mmol) was used to prepare 10.2 g (yield 86%) of [Compound 21].
합성예 6: 화합물 31의 제조Synthesis Example 6: Preparation of compound 31
합성예 6-1: 2,2',2''-((((1,3,5-트리아진-2,4,6-트릴리)트리스(아자니디닐))트리스(벤진-3,1-디닐))트리스(옥시))트리에탄올의 제조Synthesis Example 6-1: 2,2',2''-((((1,3,5-triazine-2,4,6-trily)tris(azanidinyl))tris(benzine-3,1 Preparation of -dinyl)) tris (oxy)) triethanol
250 mL 반응기에 DMF 100 ml를 넣고 질소분위기 하에서 3,3',3''-((1,3,5-트리아진-2,4,6-트라이일리)트리스(아자니디닐))트리페놀 10 g (24.9 mmol)과 K2CO3 10.3g(74.7mmol)을 가한다. 위 반응기에 2-bromoethanol 11.2g(89.5mmol)을 30분간 천천히 가한 후 80oC에서 10시간 동안 교반한다. 반응종료 후 증류수와 에틸아세테이트로 추출하여 유기물을 분리한 후 에틸아세테이트 층을 증류수로 2회 세척한다. 유기층을 MgSO4를 사용하여 수분을 제거하고, 감압 농축하여 흰색 고체 2,2',2''-((((1,3,5-트리아진-2,4,6-트릴리)트리스(아자니디닐))트리스(벤진-3,1-디닐))트리스(옥시))트리에탄올의 제조 12.8g (수율 96%)을 제조하였다.Put 100 ml of DMF into a 250 mL reactor and under nitrogen atmosphere, 3,3',3''-((1,3,5-triazine-2,4,6-trily)tris(azanidinyl))triphenol 10 g (24.9 mmol) and K 2 CO 3 10.3 g (74.7 mmol) are added. After slowly adding 11.2 g (89.5 mmol) of 2-bromoethanol to the above reactor for 30 minutes, the mixture was stirred at 80 o C for 10 hours. After completion of the reaction, the organic material was separated by extraction with distilled water and ethyl acetate, and the ethyl acetate layer was washed twice with distilled water. The organic layer was removed from moisture using MgSO 4 , and concentrated under reduced pressure to form a white solid 2,2',2''-(((1,3,5-triazine-2,4,6-trily)tris( Preparation of azanidinyl))tris(benzine-3,1-dinyl))tris(oxy))triethanol 12.8 g (yield 96%) was prepared.
합성예 6-2. 화합물 31의 제조Synthesis Example 6-2. Preparation of compound 31
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 2,2',2''-((((1,3,5-트리아진-2,4,6-트릴리)트리스(아자니디닐))트리스(벤진-3,1-디닐))트리스(옥시))트리에탄올 10.0 g (18.7 mmol), 2-(클로로메틸)-2-메틸옥시란 51.9g(561.3mmol)을 사용하여 [화합물 31] 10.6g(수율 81%)을 제조하였다.Synthesis Example 1-2 In the same manner as in the preparation of Compound 1, 100 mL of isopropyl alcohol, 2,2',2''-(((1,3,5-triazine-2,4,6-trily)tris (azanidinyl))tris(benzine-3,1-dinyl))tris(oxy))triethanol 10.0 g (18.7 mmol), 2-(chloromethyl)-2-methyloxirane 51.9 g (561.3 mmol) [Compound 31] 10.6 g (yield 81%) was prepared.
합성예 7: 화합물 36의 제조Synthesis Example 7: Preparation of compound 36
합성예 7-1. ((6-(페닐이미노)-1,3,5-트리아진-2,4-다닐)비스(아자니디닐))Synthesis Example 7-1. ((6-(phenylimino)-1,3,5-triazine-2,4-danyl)bis(azanidinyl))
디메탄올의 제조Preparation of dimethanol
합성예 3-1 과 동일한 방법으로 2,4,6-트리클로로-1,3,5-트리아진 20.0 g(108.5 mmol) 아미노메탄올 10.2 g(217.0 mmol), 아닐린10.1 g(108.5 mmol), 쇼듐아세테이트 20.0 g(244.0mmol)을 사용하여 흰색 고체 ((6-(페닐이미노)-1,3,5-트리아진-2,4-다닐)비스(아자니디닐))디메탄올 22.8g (수율 80%)을 제조하였다.In the same manner as in Synthesis Example 3-1, 2,4,6-trichloro-1,3,5-triazine 20.0 g (108.5 mmol) aminomethanol 10.2 g (217.0 mmol), aniline 10.1 g (108.5 mmol), shodium 22.8 g (yield 80) of white solid ((6-(phenylimino)-1,3,5-triazine-2,4-danyl)bis(azanidinyl))dimethanol using 20.0 g (244.0 mmol) of acetate %) was prepared.
합성예 7-2. 화합물 36의 제조Synthesis Example 7-2. Preparation of compound 36
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 2,2',2''-((((1,3,5-트리아진-2,4,6-트릴리)트리스(아자니디닐))트리스(벤진-3,1-디닐))트리스(옥시))트리에탄올 10.0 g (38.1 mmol), 2-(클로로메틸)-2-메틸옥시란 70.5g(762.0mmol)을 사용하여 [화합물 36] 12.7g(수율 89%)을 제조하였다.Synthesis Example 1-2 In the same manner as in the preparation of Compound 1, 100 mL of isopropyl alcohol, 2,2',2''-((((1,3,5-triazine-2,4,6-trily)tris(azanidinyl))tris(benzine-3,1-dinyl))tris( 12.7 g (yield 89%) of [Compound 36] was prepared using 10.0 g (38.1 mmol) of oxy)) triethanol and 70.5 g (762.0 mmol) of 2-(chloromethyl)-2-methyloxirane.
합성예 8: 화합물 37의 제조 Synthesis Example 8: Preparation of compound 37
합성예 8-1. 3,3',3'',3'''-((6,6'-(1,3-페닐렌비스(아자니디닐))비스(1,3,5-트리아진-6,4,2-드리일))테트라키스(아자니디닐))테트라페놀 의 제조Synthesis Example 8-1. 3,3',3'',3'''-((6,6'-(1,3-phenylenebis(azanidinyl))bis(1,3,5-triazine-6,4,2 Preparation of -dryl)) tetrakis (azanidinyl)) tetraphenol
합성예 3-1 과 동일한 방법으로 2,4,6-트리클로로-1,3,5-트리아진 20.0 g(108.5 mmol) 3-아미노페놀 23.7 g(217.0 mmol), 아닐린5.9 g(54.3 mmol), 쇼듐아세테이트 20.0 g(244.0mmol)을 사용하여 흰색 고체 3,3',3'',3'''-((6,6'-(1,3-페닐렌비스(아자니디닐))비스(1,3,5-트리아진-6,4,2-드리일))테트라키스(아자니디닐))테트라페놀 29.8g (수율 79%)을 제조하였다.In the same manner as in Synthesis Example 3-1, 2,4,6-trichloro-1,3,5-triazine 20.0 g (108.5 mmol) 3-aminophenol 23.7 g (217.0 mmol), aniline 5.9 g (54.3 mmol) , using 20.0 g (244.0 mmol) of shodium acetate as a white solid 3,3',3'',3'''-((6,6'-(1,3-phenylenebis(azanidinyl))bis( 1,3,5-triazine-6,4,2-triyl))tetrakis(azanidinyl))tetraphenol 29.8 g (yield 79%) was prepared.
합성예 8-2. 화합물 37의 제조Synthesis Example 8-2. Preparation of compound 37
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 3,3',3'',3'''-((6,6'-(1,3-페닐렌비스(아자니디닐))비스(1,3,5-트리아진-6,4,2-드리일))테트라키스(아자니디닐))테트라페놀 10.0 g (14.4 mmol), 2-(클로로메틸)-2-메틸옥시란 53.3g(576.0mmol)을 사용하여 [화합물 37] 11.5g(수율 87%)을 제조하였다.Synthesis Example 1-2 In the same manner as in the preparation of Compound 1, 100 mL of isopropyl alcohol, 3,3',3'',3'''-((6,6'-(1,3-phenylenebis(azanidinyl))bis(1,3,5-triazine-6,4,2 -Driyl))tetrakis(azanidinyl))tetraphenol 10.0 g (14.4 mmol), 2-(chloromethyl)-2-methyloxirane 53.3 g (576.0 mmol) [Compound 37] 11.5 g (yield) 87%) was prepared.
합성예 9: 화합물 47의 제조Synthesis Example 9: Preparation of compound 47
합성예 9-1. 4,6-디클로로-N-(4,6-디클로로-1,3,5-트리아진-2-닐)-N-페닐-1,3,5-트리아진-2-아민의 제조Synthesis Example 9-1. Preparation of 4,6-dichloro-N- (4,6-dichloro-1,3,5-triazin-2-yl)-N-phenyl-1,3,5-triazin-2-amine
500 mL 반응기에 THF 200 ml를 넣고 질소분위기 하에 2,4,6-트리클로로-1,3,5-트리아진 20.0 g(108.5 mmol)을 가한다. 반응플라스크를 0oC로 냉각한 뒤 아닐린 5.0 g(54.2 mmol)을 교반하면서 30분 동안 천천히 가한 후 쇼듐아세테이트 17.8 g(216.9 mmol)을 가한다. 상온에서 10시간 동안 교반한다. 반응종료 후 증류수 150ml를 첨가하고 교반하여 흰색 고체 4,6-디클로로-N-(4,6-디클로로-1,3,5-트리아진-2-닐)-N-페닐-1,3,5-트리아진-2-아민 17.1g (수율 81%)을 제조하였다.In a 500 mL reactor, 200 ml of THF is added, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine is added under a nitrogen atmosphere. After cooling the reaction flask to 0 o C, 5.0 g (54.2 mmol) of aniline was slowly added for 30 minutes while stirring, and then 17.8 g (216.9 mmol) of shodium acetate was added. Stir at room temperature for 10 hours. After completion of the reaction, 150 ml of distilled water was added and stirred to stir a white solid 4,6-dichloro-N-(4,6-dichloro-1,3,5-triazin-2-yl)-N-phenyl-1,3,5 - Triazin-2-amine 17.1 g (yield 81%) was prepared.
합성예 9-2. 3,3',3'',3'''-((6,6'-(페닐아자니디닐)비스(1,3,5-트리아진-6,4,2-트리일))테트라키스(아자니디닐))테트라페놀의 제조Synthesis Example 9-2. 3,3',3'',3'''-((6,6'-(phenylazanidinyl)bis(1,3,5-triazine-6,4,2-triyl))tetrakis( Preparation of azanidinyl)) tetraphenol
합성예 3-1 과 동일한 방법으로 4,6-디클로로-N-(4,6-디클로로-1,3,5-트리아진-2-닐)-N-페닐-1,3,5-트리아진-2-아민 17.1 g(43.9 mmol), 3-아미노페놀 19.2 g(175.7 mmol), 쇼듐아세테이트 14.4 g(175.7 mmol)을 사용하여 흰색 고체 3,3',3'',3'''-((6,6'-(페닐아자니디닐)비스(1,3,5-트리아진-6,4,2-트리일)) 테트라키스(아자니디닐))테트라페놀 26.9g (수율 90%)을 제조하였다.In the same manner as in Synthesis Example 3-1, 4,6-dichloro-N-(4,6-dichloro-1,3,5-triazin-2-yl)-N-phenyl-1,3,5-triazine 17.1 g (43.9 mmol) of -2-amine, 19.2 g (175.7 mmol) of 3-aminophenol, and 14.4 g (175.7 mmol) of sodium acetate were used as a white solid 3,3',3'',3'''-( 26.9 g of (6,6'-(phenylazanidinyl)bis(1,3,5-triazine-6,4,2-triyl))tetrakis(azanidinyl))tetraphenol (yield 90%) was prepared did.
합성예 9-3. 화합물 47의 제조Synthesis Example 9-3. Preparation of compound 47
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 3,3',3'',3'''-((6,6'-(페닐아자니디닐)비스(1,3,5-트리아진-6,4,2-트리일))테트라키스(아자니디닐))테트라페놀 9.8 g (14.4 mmol), 2-(클로로메틸)-2-메틸옥시란 53.3g(576.0mmol)을 사용하여 [화합물 47] 11.2g(수율 86%)을 제조하였다.Synthesis Example 1-2 100 mL of isopropyl alcohol, 3,3',3'',3'''-((6,6'-(phenylazanidinyl)bis(1,3, 5-triazine-6,4,2-triyl))tetrakis(azanidinyl))tetraphenol 9.8 g (14.4 mmol), 2-(chloromethyl)-2-methyloxirane 53.3 g (576.0 mmol) 11.2 g (yield 86%) of [Compound 47] was prepared using
합성예 10: 화합물 51의 제조Synthesis Example 10: Preparation of compound 51
합성예 10-1. 4,6-디클로로-N-(4,6-디클로로-1,3,5-트리아진-2-닐)-N-페닐-1,3,5-트리아진-2-아민의 제조Synthesis Example 10-1. Preparation of 4,6-dichloro-N- (4,6-dichloro-1,3,5-triazin-2-yl)-N-phenyl-1,3,5-triazin-2-amine
500 mL 반응기에 THF 200 ml를 넣고 질소분위기 하에 2,4,6-트리클로로-1,3,5-트리아진 20.0 g(108.5 mmol), 페놀 11.2 g(119.4 mmol)을 가한다. 반응플라스크를 0oC로 냉각한 뒤, 강소다(쇼듐하이드록시드) 6.5g(162.8 mmol)을 증류수 50ml에 용해한 후 교반하면서 30분 동안 천천히 가한 후 서서히 상온으로 승온하여 3시간 동안 교반한 뒤, 증류수를 가하여 흰색 고체 2,4-디클로로-6-페녹시-1,3,5-트리아진 11.8g (수율 45%)을 제조하였다.Put 200 ml of THF in a 500 mL reactor, and 20.0 g (108.5 mmol) of 2,4,6-trichloro-1,3,5-triazine and 11.2 g (119.4 mmol) of phenol are added under a nitrogen atmosphere. After the reaction flask was cooled to 0 o C, 6.5 g (162.8 mmol) of strong sodium hydroxide (sodium hydroxide) was dissolved in 50 ml of distilled water, added slowly for 30 minutes while stirring, and then slowly raised to room temperature and stirred for 3 hours. , distilled water was added to prepare 11.8 g (yield 45%) of white solid 2,4-dichloro-6-phenoxy-1,3,5-triazine.
합성예 10-2. 3,3'-((6-페녹시-1,3,5-트리아진-2,4-디닐)비스(아자니디닐))디페놀의 제조Synthesis Example 10-2. Preparation of 3,3'-((6-phenoxy-1,3,5-triazine-2,4-dinyl)bis(azanidinyl))diphenol
합성예 3-1 과 동일한 방법으로 2,4-디클로로-6-페녹시-1,3,5-트리아진 10.6 g(43.9 mmol), 3-아미노페놀 9.6 g(87.8 mmol), 쇼듐아세테이트 8.0 g(87.8 mmol)을 사용하여 흰색 고체 3,3'-((6-페녹시-1,3,5-트리아진-2,4-디닐)비스(아자니디닐))디페놀 15.1g (수율 89%)을 제조하였다.In the same manner as in Synthesis Example 3-1, 2,4-dichloro-6-phenoxy-1,3,5-triazine 10.6 g (43.9 mmol), 3-aminophenol 9.6 g (87.8 mmol), shodium acetate 8.0 g (87.8 mmol) as a white solid 3,3'-((6-phenoxy-1,3,5-triazine-2,4-dinyl)bis(azanidinyl))diphenol 15.1 g (yield 89%) ) was prepared.
합성예 10-3. 화합물 51의 제조Synthesis Example 10-3. Preparation of compound 51
합성예 1-2 화합물1의 제조와 동일한 방법으로 이소프로필알콜 100mL, 3,3'-((6-페녹시-1,3,5-트리아진-2,4-디닐)비스(아자니디닐))디페놀 5.6 g (14.4 mmol), 2-(클로로메틸)-2-메틸옥시란 26.7g(288.0mmol)을 사용하여 [화합물 51] 6.3g(수율 87%)을 제조하였다.Synthesis Example 1-2 In the same manner as in the preparation of Compound 1, 100 mL of isopropyl alcohol, 3,3'-((6-phenoxy-1,3,5-triazine-2,4-dinyl)bis(azanidinyl) ) Diphenol 5.6 g (14.4 mmol) and 2-(chloromethyl)-2-methyloxirane 26.7 g (288.0 mmol) were used to prepare 6.3 g (yield 87%) of [Compound 51].
실시예 1 내지 13 Examples 1 to 13
하기 표 1의 조성에 따라, (A) 고굴절에폭시 모노머, (B) 광중합성 모노머, (C) 광개시제(광산발생제) D) UV안정제를 하기 표 1에 기재된 조성비로 갈색 반응기에 넣고 10 시간 동안 교반하여 감광성 조성물을 제조하였다.According to the composition of Table 1 below, (A) high refractive epoxy monomer, (B) photopolymerizable monomer, (C) photoinitiator (photoacid generator) D) UV stabilizer at the composition ratio shown in Table 1 below, put into a brown reactor and for 10 hours A photosensitive composition was prepared by stirring.
실시예 1 내지 13 및 비교예 1 내지 2에서 사용한 첨가제의 종류는 하기에 기재된 바와 같다.The types of additives used in Examples 1 to 13 and Comparative Examples 1 to 2 are as described below.
(A) 에폭시기 포함 모노머(A) Epoxy group-containing monomer
화합물1 (M1): N2,N4,N6-트리스(3-(옥시란-2-닐메톡시)페닐)-1,3,5-트리아진-2,4,6-트라이아민Compound 1 (M1): N2,N4,N6-tris(3-(oxiran-2-ylmethoxy)phenyl)-1,3,5-triazine-2,4,6-triamine
화합물3 (M3): 3,3'-((6-((3-(옥시란-2-닐메톡시)페닐)아미노)-1,3,5-트리아진-2,4-디닐)비스(아잔디닐))디페놀Compound 3 (M3): 3,3'-((6-((3-(oxiran-2-ylmethoxy)phenyl)amino)-1,3,5-triazine-2,4-dinyl)bis( Azandinyl)) Diphenol
화합물5 (M5): N2-(3-(옥시란-2-일메톡시)페닐)-N4,N6-디페닐-1,3,5-트리아진-2,4,6-트리아민Compound 5 (M5): N2-(3-(oxiran-2-ylmethoxy)phenyl)-N4,N6-diphenyl-1,3,5-triazine-2,4,6-triamine
화합물13 (M13): N2,N4-비스(3-(옥시란-2-닐메톡시)페닐)-6-(페닐티오)-1,3,5-트리아진-2,4-디아민Compound 13 (M13): N2,N4-bis(3-(oxiran-2-ylmethoxy)phenyl)-6-(phenylthio)-1,3,5-triazine-2,4-diamine
화합물31 (M31): N2,N4,N6-tris(3-(2-(옥시란-2-닐메톡시)에톡시)페닐)-1,3,5-트리아진-2,4,6-트리아민Compound 31 (M31): N2,N4,N6-tris(3-(2-(oxiran-2-ylmethoxy)ethoxy)phenyl)-1,3,5-triazine-2,4,6-tri amine
화합물36 (M36): N2,N4-bis((옥시란-2-닐메톡시)메틸)-N6-페닐-1,3,5-트리아진-2,4,6-트리아민Compound 36 (M36): N2,N4-bis((oxiran-2-ylmethoxy)methyl)-N6-phenyl-1,3,5-triazine-2,4,6-triamine
화합물37 (M37): N2,N2'-(1,3-페닐렌)비스(N4,N6-비스(3-(옥시란-2-닐메톡시)페닐)-1,3,5-트리아진-2,4,6-트리아민)Compound 37 (M37): N2,N2'-(1,3-phenylene)bis(N4,N6-bis(3-(oxiran-2-ylmethoxy)phenyl)-1,3,5-triazine- 2,4,6-triamine)
화합물47 (M47): N2-(4,6-비스((3-(옥시란-2-닐메톡시)페닐)아미노)-1,3,5-트리아진-2-일)-N4,N6-비스(3-(옥시란-2-닐메톡시)페닐)-N2-페닐-1,3,5-트리아진-2,4,6-트리아민Compound 47 (M47): N2-(4,6-bis((3-(oxiran-2-ylmethoxy)phenyl)amino)-1,3,5-triazin-2-yl)-N4,N6- Bis(3-(oxiran-2-ylmethoxy)phenyl)-N2-phenyl-1,3,5-triazine-2,4,6-triamine
화합물51 (M51): N2,N4-비스(3-(옥시란-2-닐메톡시)페닐)-6-페녹시-1,3,5-트리아진-2,4-디아민Compound 51 (M51): N2,N4-bis(3-(oxiran-2-ylmethoxy)phenyl)-6-phenoxy-1,3,5-triazine-2,4-diamine
(B) 광중합성 화합물(B) photopolymerizable compound
B1 : 2-비페닐 글리시디닐 에테르B1: 2-biphenyl glycidinyl ether
B2 : 글리시디닐 4-메톡시페닐 에테르B2: glycidinyl 4-methoxyphenyl ether
(C) 광중합 개시제(C) photoinitiator
PA1)
(D) UV안정제(D) UV stabilizer
E1 : 아민계 UV 안정제 E1: Amine-based UV stabilizer
비교예 1 내지 비교예 2Comparative Examples 1 to 2
실시예 1과 실시예 2에서 고굴절모노머를 화합물 1(M1) 대신에 하기 R1 2,2'-((((9H-플루오렌-9,9-다닐)비스(4,1-페닐렌)) 비스(옥시))비스(메틸렌)) 비스(옥시란)를 사용한 것을 제외하고는 동일한 방법으로 제조하였다.In Examples 1 and 2, the high refractive monomer was replaced with Compound 1 (M1) to the following R1 2,2'-((((9H-fluorene-9,9-danyl)bis(4,1-phenylene)) Bis(oxy))bis(methylene)) It was prepared in the same manner except that bis(oxirane) was used.
R1)
실험예 1: 굴절율 평가Experimental Example 1: Evaluation of refractive index
합성된 고굴절 에폭시모노머를 2-비페닐 글리시디닐 에테르와 같이 굴절률이 알려진 모노머에 동일량의 무게비로 녹인 후 25oC에서 ABBE 굴절계로 측정할 수 있다. 실시예에서는 제조된 조성물을 25oC에서 ABBE 굴절계로 측정하였다.The synthesized high refractive epoxy monomer can be dissolved in a monomer with a known refractive index, such as 2-biphenyl glycidinyl ether, in the same amount by weight, and then measured with an ABBE refractometer at 25 o C. In the example, the prepared composition was measured with an ABBE refractometer at 25 o C.
실험예 2: 투과도 평가Experimental Example 2: Permeability evaluation
광학용 PET 기판 위에 500 mJ/cm2으로 UV 조사하여 가교된 프리즘 시트 시편을 제조하였다. 가교된 프리즘 시트를 UV-vis을 사용하여 400 nm에서 UV 투과도를 측정하였다. A crosslinked prism sheet specimen was prepared by UV irradiation at 500 mJ/cm 2 on the optical PET substrate. The crosslinked prism sheet was measured for UV transmittance at 400 nm using UV-vis.
실험예 3: 항변지수(△YI) 평가Experimental Example 3: Antivariance index (ΔYI) evaluation
가교된 프리즘 시트를 신뢰성 평가 설비 (QUV tester)를 사용하여 60℃에서 UVA lamp 1J 8시간 습도 95% 조건으로 8시간을 반복하여 120시간 동안 진행한 후 초기 Yellow Index값 대비 변화수치인 △YI 값을 측정하였다.After repeating the crosslinked prism sheet for 120 hours by repeating the cross-linked prism sheet at 60°C under the condition of UVA lamp 1J for 8 hours and 95% humidity for 120 hours using a reliability evaluation facility (QUV tester), ΔYI value, which is a change value compared to the initial Yellow Index value was measured.
평가 결과는 하기 표 3에 기재하였다.The evaluation results are shown in Table 3 below.
상기 표 3에 나타난 바와 같이, 본 발명의 실시예 1 내지 13의 감광성 조성물은 비교예 1 내지 2의 조성물에 비해 현저히 높은 굴절율을 나타내었다. 프리즘 시트로 평가한 결과 비교예 1 내지 2의 조성물에 비해 광 투과율이 우수하였으며, 신뢰성 평가 후의 황변 특성이 우수함을 확인하였다. As shown in Table 3, the photosensitive compositions of Examples 1 to 13 of the present invention exhibited a significantly higher refractive index than the compositions of Comparative Examples 1 to 2. As a result of evaluation with the prism sheet, it was confirmed that the light transmittance was excellent compared to the compositions of Comparative Examples 1 and 2, and the yellowing property after reliability evaluation was excellent.
이상에서 본 발명의 바람직한 실시예들에 대하여 상세하게 설명하였지만 본 발명의 권리 범위는 이에 한정되는 것은 아니고 다음의 청구 범위에서 정의하고 있는 본 발명의 기본 개념을 이용한 당업자의 여러 변형 및 개량 형태 또한 본 발명의 권리 범위에 속하는 것이다.Although preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims are also present. It belongs to the scope of the invention.
Claims (24)
[화학식 B]
[화학식 C]
상기 [화학식 B] 및 [화학식 C]에서,
상기 L4 내지 L9는 각각 동일하거나 상이하며, 서로 독립적으로 단일 결합, O, S, -N(-R21)- 중에서 선택된 어느 하나이며,
상기 L4 내지 L9 중 2 이상이 각각 -N(-R21)- 를 선택하는 경우에 각각의 -N(-R21)-는 동일하거나 상이하며,
상기 W4 내지 W7은 각각 동일하거나 상이하며, 서로 독립적으로 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1-C12의 알킬렌기 중에서 선택되는 어느 하나이고,
상기 X4 내지 X7는 동일하거나 상이하며, 서로 독립적으로 O, S, -N(-R22)-, -O((CH2)mO)n- 중에서 선택된 어느 하나이되,
상기 m 및 n은 각각 동일하거나 상이하며, 서로 독립적으로 1 내지 4 중에서 선택되는 정수이고,
상기 X4 내지 X7 중 2 이상이 각각 -N(-R22)- 를 선택하거나 또는 상기 X4 내지 X7 중 2 이상이 각각 -O((CH2)mO)n-를 선택하는 경우에 각각의 -N(-R22)- 및 -O((CH2)mO)n-는 각각 동일하거나 상이하며,
상기 R21 및 R22는 각각 동일하거나 상이하며, 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C50의 아릴기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C7-C24의 아릴알킬기 중에서 선택된 어느 하나이고,
상기 E4 내지 E7는 서로 동일하거나 상이하며, 서로 독립적으로 수소, 중수소 치환 또는 비치환된 C1-C30의 알킬기, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C2-C30의 알케닐기, 치환 또는 비치환된 C2-C20의 알키닐기, 치환 또는 비치환된 C3-C30의 시클로알킬기, 치환 또는 비치환된 C5-C30의 시클로알케닐기, 치환 또는 비치환된 C2-C50의 헤테로아릴기, 치환 또는 비치환된 C2-C30의 헤테로시클로알킬기, 치환 또는 비치환된 C1-C30의 알킬실릴기, 치환 또는 비치환된 C6-C30의 아릴실릴기 및 하기 [구조식 a] 또는 [구조식 b]로 표시되는 치환기 중에서 선택된 어느 하나이되,
상기 E4 내지 E7 중 적어도 하나는 [구조식 a] 또는 [구조식 b]로 표시되는 치환기이고,
[구조식 a]
[구조식 b]
상기 [구조식 a] 및 [구조식 b]에서,
상기 R4, R7 및 R11 은 각각 동일하거나 상이하며, 서로 독립적으로 치환 또는 비치환된 C1-C12의 알킬렌기, 치환 또는 비치환된 C6-C30의 아릴렌기 중에서 선택되는 어느 하나이고,
상기 R5, R6, R8 내지 R10, R12 내지 R14 은 각각 동일하거나 상이하며, 서로 독립적으로 수소, 중수소, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기 중에서 선택되는 어느 하나이며,
상기 구조식 a 및 구조식 b 내 “-*”는 각각 상기 화학식 B 및 화학식 C 내 X4 내지 X7 중에서 어느 하나와 결합되는 결합 사이트를 의미하고,
상기 [화학식 B] 에서,
상기 Ra는 치환 또는 비치환된 C6-C30의 아릴렌기, 치환 또는 비치환된 C1- C12의 알킬렌기 중에서 선택되는 어느 하나이며,
상기 X4는 -O- 이고, 상기 W4이 치환 또는 비치환된 페닐렌기이며, 상기 X4은 L4 을 기준으로 오르쏘 또는 메타 위치에 치환되거나;
또는, 상기 X5 는 -O- 이고, 상기 W 5이 치환 또는 비치환된 페닐렌기이며, 상기 X5 은 L5을 기준으로 오르쏘 또는 메타 위치에 치환되거나;
또는, 상기 X6 는 -O- 이고, 상기 W6이 치환 또는 비치환된 페닐렌기이며, 상 기 X6은 L5을 기준으로 오르쏘 또는 메타 위치에 치환되거나;
또는, 상기 X 7 는 -O- 이고, 상기 W7이 치환 또는 비치환된 페닐렌기이며, 상기 X7은 L7을 기준으로 오르쏘 또는 메타 위치에 치환되며,
상기 [화학식 C]에서,
상기 Ra'은 수소, 중수소 , 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기 중에서 선택되는 어느 하나이고,
상기 [화학식 B] 내지 [화학식 C]에서의 ‘치환 또는 비치환된’에서의‘치환’은 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, C1-C24의 알킬기, C1-C24의 할로겐화된 알킬기, C2-C24의 알케닐기, C2-C24의 알키닐기, C1-24의 헤테로알킬기, C6-C24의 아릴기, C7-C24의 아릴알킬기, C2-C24의 헤테로아릴기, C2-C24의 헤테로아릴알킬기, C1-C24의 알콕시기, C1-C24의 알킬티오닐기, C1-C24의 알킬아미노기, C6-C24의 아릴아미노기, C1-C24의 헤테로 아릴아미노기, C1-C24의 알킬실릴기, C6-C24의 아릴실릴기, C6-C24의 아릴옥시기, C6-C24의 아릴티오닐기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되는 것을 의미한다.
A compound represented by any one of the following [Formula B] to [Formula C].
[Formula B]
[Formula C]
In the [Formula B] and [Formula C],
The L 4 to L 9 are the same or different from each other, and are each independently any one selected from a single bond, O, S, -N(-R 21 )-,
When two or more of L 4 to L 9 each select -N(-R 21 )-, each -N(-R 21 )- is the same or different,
Each of W 4 to W 7 are the same or different, and are each independently selected from a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C1-C12 alkylene group,
Wherein X 4 To X 7 Are the same or different, and each independently be any one selected from O, S, -N(-R 22 )-, -O((CH 2 ) m O) n -,
Wherein m and n are the same or different from each other, and independently of each other are integers selected from 1 to 4,
When two or more of X 4 to X 7 each select -N(-R 22 )-, or two or more of X 4 to X 7 each select -O((CH 2 ) m O) n - to each -N(-R 22 )- and -O((CH 2 ) m O) n - are each the same or different,
wherein R 21 and R 22 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C3- Any one selected from a C30 cycloalkyl group, a substituted or unsubstituted C7-C24 arylalkyl group,
E 4 to E 7 are the same as or different from each other, and independently of each other hydrogen, deuterium substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 of an alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 A heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, and the following [Structural formula a] or [ Any one selected from the substituents represented by Structural Formula b],
At least one of E 4 to E 7 is a substituent represented by [Structural Formula a] or [Structural Formula b],
[Structural formula a]
[Structural formula b]
In the [Structural Formula a] and [Structural Formula b],
Wherein R 4, R 7 and R 11 is one in which each the same or different and are each independently selected from a substituted or unsubstituted arylene group, a C1-C12 alkylene group, a substituted or unsubstituted C 6 -C 30 ,
The R 5 , R 6 , R 8 To R 10 , R 12 to R 14 are the same or different, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C1-C12 alkyl group,
“-*” in Structural Formulas a and b means a binding site bonded to any one of X 4 to X 7 in Formula B and Formula C, respectively,
In the [Formula B],
Wherein Ra is any one selected from a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C1-C12 alkylene group,
wherein X 4 is —O—, W 4 is a substituted or unsubstituted phenylene group, and X 4 is ortho or meta-substituted with respect to L 4 ;
Alternatively, X 5 is —O—, W 5 is a substituted or unsubstituted phenylene group, and X 5 is ortho or meta-substituted with respect to L 5 ;
Alternatively, X 6 is -O-, W 6 is a substituted or unsubstituted phenylene group , wherein X 6 is ortho or meta-substituted with respect to L 5 ;
Alternatively, X 7 is -O-, wherein W 7 is a substituted or unsubstituted phenylene group, wherein X 7 is substituted at an ortho or meta position with respect to L 7 ,
In the [Formula C],
Wherein Ra' is any one selected from hydrogen, deuterium, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C1-C12 alkyl group,
'Substitution' in 'substituted or unsubstituted' in [Formula B] to [Formula C] is deuterium, cyano group, halogen group, hydroxyl group, nitro group, C1-C24 alkyl group, C1-C24 halogenated Alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-24 heteroalkyl group, C6-C24 aryl group, C7-C24 arylalkyl group, C2-C24 heteroaryl group, C2-C24 hetero Arylalkyl group, C1-C24 alkoxy group, C1-C24 alkylthionyl group, C1-C24 alkylamino group, C6-C24 arylamino group, C1-C24 hetero arylamino group, C1-C24 alkylsilyl group, C6 -C24 arylsilyl group, C6-C24 aryloxy group, C6-C24 arylthionyl group means substituted with one or more substituents selected from the group consisting of.
상기 [화학식 B] 및 [화학식 C]에서,
상기 L4 내지 L7 중에서 2 이상은 각각 S 또는 -N(-R21)- 이고,
상기 R21은 수소, 중수소, 치환 또는 비치환된 C6-C30의 아릴기, 치환 또는 비치환된 C1-C12의 알킬기에서 선택되는 어느 하나인 것을 특징으로 하는 화합물.
여기서, 상기 L4 내지 L7 중에서 2 이상이 -N(-R21)- 인 경우에 각각의 -N(-R21)-는 각각 동일하거나 상이하다.
According to claim 1,
In the [Formula B] and [Formula C],
2 or more of L 4 to L 7 are each S or -N(-R 21 )-,
wherein R 21 is hydrogen, deuterium, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C1-C12 alkyl group.
Here, when two or more of L 4 to L 7 are -N(-R 21 )-, each -N(-R 21 )- is the same or different from each other.
상기 [화학식 B] 및 [화학식 C]에서,
상기 L4 내지 L7 은 각각 동일하거나 상이하며, 서로 독립적으로 S 또는 -N(-R21)- 인 것을 특징으로 하는 화합물.
여기서, 상기 L4 내지 L7 중에서 2 이상이 -N(-R21)- 인 경우에 각각의 -N(-R21)-는 각각 동일하거나 상이하다.
11. The method of claim 10,
In the [Formula B] and [Formula C],
The L 4 to L 7 are the same or different from each other, and each independently S or -N(-R 21 )- A compound, characterized in that.
Here, when two or more of L 4 to L 7 are -N(-R 21 )-, each -N(-R 21 )- is the same or different from each other.
상기 [화학식 B] 및 [화학식 C]에서,
상기 R21는 각각 수소 또는 중수소인 것을 특징으로 하는 화합물.
11. The method of claim 10,
In the [Formula B] and [Formula C],
Wherein R 21 is a compound, characterized in that each hydrogen or deuterium.
상기 [화학식 C]에서,
상기 X4는 -O- 이고, 상기 W4이 치환 또는 비치환된 페닐렌기이며, 상기 X4은 L4을 기준으로 오르쏘 또는 메타 위치에 치환되거나;
또는, 상기 X5 는 -O- 이고, 상기 W5이 치환 또는 비치환된 페닐렌기이며, 상기 X5은 L5을 기준으로 오르쏘 또는 메타 위치에 치환되거나;
또는, 상기 X6 는 -O- 이고, 상기 W6이 치환 또는 비치환된 페닐렌기이며, 상기 X6은 L5을 기준으로 오르쏘 또는 메타 위치에 치환되거나;
또는, 상기 X7 는 -O- 이고, 상기 W7이 치환 또는 비치환된 페닐렌기이며, 상기 X7은 L7을 기준으로 오르쏘 또는 메타 위치에 치환되는 것을 특징으로 하는 화합물.
According to claim 1,
In the [Formula C],
wherein X 4 is —O—, W 4 is a substituted or unsubstituted phenylene group, and X 4 is ortho or meta-substituted with respect to L 4 ;
Alternatively, X 5 is —O—, W 5 is a substituted or unsubstituted phenylene group, and X 5 is ortho or meta-substituted with respect to L 5 ;
Alternatively, X 6 is -O-, W 6 is a substituted or unsubstituted phenylene group, wherein X 6 is ortho or meta-substituted with respect to L 5 ;
Alternatively, X 7 is -O-, W 7 is a substituted or unsubstituted phenylene group, and X 7 is a compound characterized in that it is substituted at an ortho or meta position with respect to L 7 .
상기 [화학식 B] 및 [화학식 C]내 W4 내지 W7 중에서 2 이상은 치환 또는 비치환된 C6-C30의 아릴렌기인 것을 특징으로 하는 화합물.
According to claim 1,
2 or more of W 4 to W 7 in [Formula B] and [Formula C] is a substituted or unsubstituted C 6 -C 30 A compound, characterized in that it is an arylene group.
상기 [화학식 B] 및 [화학식 C]내 W4 내지 W7 중에서 3 이상은 치환 또는 비치환된 C6-C30의 아릴렌기인 것을 특징으로 하는 화합물.
15. The method of claim 14,
3 or more of W 4 to W 7 in [Formula B] and [Formula C] is a substituted or unsubstituted C 6 -C 30 A compound, characterized in that it is an arylene group.
상기 [화학식 B] 및 [화학식 C]내 W4 내지 W7 중에서 2 이상은 치환 또는 비치환된 페닐렌기인 것을 특징으로 하는 화합물.
15. The method of claim 14,
2 or more of W 4 to W 7 in [Formula B] and [Formula C] are a substituted or unsubstituted phenylene group.
상기 [화학식 B] 및 [화학식 C]내 W4 내지 W7 중에서 3 이상은 치환 또는 비치환된 페닐렌기인 것을 특징으로 하는 화합물.
17. The method of claim 16,
3 or more of W 4 to W 7 in [Formula B] and [Formula C] is a substituted or unsubstituted phenylene group.
상기 [화학식 C]에서 X4 내지 X7 중 적어도 1개는 O 인 것을 특징으로 하는 화합물.
According to claim 1,
In the [Formula C], at least one of X 4 to X 7 is O. A compound characterized in that.
상기 [화학식 B] 내지 [화학식 C]로 표시되는 화합물은 하기 화합물 37 내지 50 중에서 선택된 어느 하나로 표시되는 것을 특징으로 하는 화합물.
<화합물 37> <화합물 38>
<화합물 39> <화합물 40>
<화합물 41> <화합물 42>
<화합물 43> <화합물 44>
<화합물 45> <화합물 46>
<화합물 47> <화합물 48>
<화합물 49> <화합물 50>
According to claim 1,
The compound represented by the [Formula B] to [Formula C] is a compound, characterized in that represented by any one selected from the following compounds 37 to 50.
<Compound 37><Compound38>
<Compound 39><Compound40>
<Compound 41><Compound42>
<Compound 43><Compound44>
<Compound 45><Compound46>
<Compound 47><Compound48>
<Compound 49><Compound50>
A photosensitive or thermosetting composition comprising the compound according to any one of claims 1 to 19.
상기 조성물은 광개시제, 열개시제 광중합성 모노머 또는 열중합성 모노머를 추가적으로 포함하는 것을 특징으로 하는 감광성 또는 열경화성 조성물.
21. The method of claim 20,
The composition is a photosensitive or thermosetting composition, characterized in that it additionally comprises a photoinitiator, a thermal initiator photopolymerizable monomer or a thermally polymerizable monomer.
An optical material obtained by polymerizing the composition of claim 21.
With respect to 100 parts by weight of the photosensitive composition, claims 1 to 95 parts by weight of the compound according to any one of claims 10 to 19, 0 to 90 parts by weight of a photopolymerizable monomer, and 0.1 to 20 parts by weight of a photoinitiator. Characterized in the photosensitive composition.
상기 조성물은 프리즘시트, 마이크로렌즈, DBEF 필름, LCD용 코팅 재료, 유기발광소자(OLED)용 코팅 재료, 광학렌즈, 다초점렌즈 중에서 선택되는 어느 하나를 제조하기 위해 사용되는 것을 특징으로 하는 감광성 또는 열경화성 조성물.21. The method of claim 20,
The composition is a photosensitive or thermosetting composition.
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